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[ CAS No. 77611-37-1 ] {[proInfo.proName]}

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Cat. No.: {[proInfo.prAm]}
Chemical Structure| 77611-37-1
Chemical Structure| 77611-37-1
Structure of 77611-37-1 * Storage: {[proInfo.prStorage]}
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Product Details of [ 77611-37-1 ]

CAS No. :77611-37-1 MDL No. :MFCD01862292
Formula : C11H21NO5 Boiling Point : -
Linear Structure Formula :- InChI Key :BRFDKSWARKFUGQ-QMMMGPOBSA-N
M.W : 247.29 Pubchem ID :11368613
Synonyms :

Calculated chemistry of [ 77611-37-1 ]

Physicochemical Properties

Num. heavy atoms : 17
Num. arom. heavy atoms : 0
Fraction Csp3 : 0.82
Num. rotatable bonds : 9
Num. H-bond acceptors : 5.0
Num. H-bond donors : 3.0
Molar Refractivity : 62.44
TPSA : 95.86 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -7.13 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.54
Log Po/w (XLOGP3) : 0.95
Log Po/w (WLOGP) : 1.13
Log Po/w (MLOGP) : 0.61
Log Po/w (SILICOS-IT) : 0.53
Consensus Log Po/w : 0.95

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 0.0
Bioavailability Score : 0.56

Water Solubility

Log S (ESOL) : -1.38
Solubility : 10.4 mg/ml ; 0.0419 mol/l
Class : Very soluble
Log S (Ali) : -2.55
Solubility : 0.697 mg/ml ; 0.00282 mol/l
Class : Soluble
Log S (SILICOS-IT) : -1.3
Solubility : 12.3 mg/ml ; 0.0497 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 2.0
Synthetic accessibility : 2.87

Safety of [ 77611-37-1 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 77611-37-1 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 77611-37-1 ]

[ 77611-37-1 ] Synthesis Path-Downstream   1~85

  • 1
  • [ 6033-32-5 ]
  • [ 24424-99-5 ]
  • [ 77611-37-1 ]
YieldReaction ConditionsOperation in experiment
With triethylamine; In tetrahydrofuran; water; I. L-N-t-Boc-epsilon-hydroxynorleucine, 17: A 250-ml roundbottom flask equipped with a magnetic stirring bar was charged with 3.58 g (24.32 mmoles) of L-epsilon-hydroxynorleucine 14 and 120 ml of tetrahydrofuran/water (1:1, v/v). The mixture was stirred at RT until all of the solid had dissolved and 3.4 ml (2.47 g, 24.39 mmoles) of triethylamine was added. After 5 min, 6.37 g (29.18 mmoles) of di-tert-butyl dicarbonate in 10 ml of tetrahydrofuran was added and the solution stirred vigorously at RT overnight. The reaction mixture was concentrated in vacuo to remove tetrahydrofuran, and 30 ml of 1N aqueous sodium hydroxide was added. The solution was transferred to a 500-ml separatory funnel, extracted with ethyl acetate (2*25 ml), and the aqueous phase adjusted to pH 3.0 with solid citric acid. The solution was extracted with ethyl acetate (4*50ml), and the combined extracts dried over anhydrous sodium sulfate, filtered, and concentrated in vacuo to yield 1.8 g of a white solid, L- N-t-Boc-epsilon-hydroxynorleucine, 17.
130 mg With sodium hydrogencarbonate; sodium carbonate; In tetrahydrofuran; water; for 23h;pH 5 - 9; Into a flask were added alcohol 14 (139 mg, 0.538 mmol, 1 equiv) and THF (1.3 mL, 0.4 M). In a separate vial, sodium hydroxide (65 mg, 1.61 mmol, 3 equiv) was dissolved in water (1.3 mL). This solution was added to the THF mixture (final concentration = 0.2 M), and the mixture was stirred (22 h). To the mixture were added water (0.3 mL) and sodium bicarbonate (181 mg, 2.15 mmol, 4 equiv, giving a suspension with pH = 10). In a separate vial, di-tert-butyl dicarbonate (176 mg, 0.807 mmol, 1.5 equiv) was dissolved in THF (0.3 mL). This solution was added to the reaction mixture, which was stirred (1 h, giving pH = 5). To the mixture was added sodium carbonate (saturated aqueous, 0.2 mL, giving pH = 9). The mixture was stirred (additional 22 h), diluted with water (10 mL), washed with EtOAc (2 x 10 mL), acidified with sodium bisulfate (1 M aqueous, 6 mL, giving pH = 2), and extracted with EtOAc (3 x 10 mL). Volatiles were removed under reduced pressure to yield pure carbamate 16 (130 mg, 0.526 mmol, 98% yield). Compound analysis is consistent with published data. 1 H NMR (CDCl3 , 200 MHz) delta 5.20 (d, J = 7.0 Hz, 1H, NH), 4.40-4.11 (m, 2H, alpha, OH), 3.67 (t, J = 5.3 Hz, 2H, epsilon), 1.95-1.13 (m, 6H, 3 x CH 2 ), 1.43 (s, 9H, tBu). MS calculated for [C 11 H 21 NO 5 Na] + , requires m/z = 270.13, found m/z = 270.1 (ESI). Optical Rotation (MeOH, c = 1.1 g/dL) [alpha] D = +12.5
  • 3
  • [ 71432-55-8 ]
  • [ 77611-37-1 ]
  • [ 213176-15-9 ]
  • 5
  • [ 54244-58-5 ]
  • [ 77611-37-1 ]
  • [ 398526-17-5 ]
  • 6
  • [ 77611-37-1 ]
  • [ 149603-82-7 ]
  • [ 398526-18-6 ]
  • 7
  • [ 77611-37-1 ]
  • (S)-2-((S)-2-Amino-3-propoxy-propionylamino)-3-(4-hydroxy-phenyl)-propionic acid methyl ester [ No CAS ]
  • [ 398526-19-7 ]
  • 8
  • [ 6638-79-5 ]
  • [ 77611-37-1 ]
  • [5-hydroxy-1-(methoxy-methyl-carbamoyl)-pentyl]-carbamic acid <i>tert</i>-butyl ester [ No CAS ]
  • 9
  • [ 24205-25-2 ]
  • [ 77611-37-1 ]
  • [ 946847-80-9 ]
  • 10
  • [ 77611-37-1 ]
  • [ 946847-87-6 ]
  • 11
  • [ 77611-37-1 ]
  • [ 946847-89-8 ]
  • 12
  • [ 77611-37-1 ]
  • [ 946847-91-2 ]
  • 13
  • [ 77611-37-1 ]
  • [ 946847-92-3 ]
  • 14
  • [ 77611-37-1 ]
  • C30H45N9O6 [ No CAS ]
  • 15
  • [ 77611-37-1 ]
  • [ 946847-94-5 ]
  • 16
  • [ 77611-37-1 ]
  • C47H71N10O11P [ No CAS ]
  • 17
  • [ 77611-37-1 ]
  • C49H73N10O12P [ No CAS ]
  • 18
  • [ 77611-37-1 ]
  • C41H57N10O12P [ No CAS ]
  • 19
  • [ 77611-37-1 ]
  • C21H40N2O9S [ No CAS ]
  • 20
  • [ 77611-37-1 ]
  • C20H37N5O6 [ No CAS ]
  • 21
  • [ 77611-37-1 ]
  • [ 946847-81-0 ]
  • 22
  • [ 77611-37-1 ]
  • [ 946847-82-1 ]
  • 23
  • [ 77611-37-1 ]
  • [ 946847-84-3 ]
  • 24
  • [ 77611-37-1 ]
  • [ 474081-22-6 ]
  • 25
  • [ 77611-37-1 ]
  • (S)-2-Amino-6-hydroxy-1-thiazol-2-yl-hexan-1-one; compound with trifluoro-acetic acid [ No CAS ]
  • 26
  • [ 77611-37-1 ]
  • ((10S)-isopropyl-(13S)-[(R)-oxiranyl]-8,11-dioxo-2-oxa-9,12-diaza-bicyclo[13.2.2]nonadeca-1(18),15(19),16-trien-(7S)-yl)-carbamic acid tert-butyl ester [ No CAS ]
  • 27
  • [ 77611-37-1 ]
  • (7S,10S,13S)-7-tert-Butoxycarbonylamino-10-isopropyl-8,11-dioxo-2-oxa-9,12-diaza-bicyclo[13.2.2]nonadeca-1(18),15(19),16-triene-13-carboxylic acid methyl ester [ No CAS ]
  • 28
  • [ 77611-37-1 ]
  • [ 398526-20-0 ]
  • 29
  • [ 77611-37-1 ]
  • [(7S,10S,13S)-13-(2-Bromo-acetyl)-10-isopropyl-8,11-dioxo-2-oxa-9,12-diaza-bicyclo[13.2.2]nonadeca-1(18),15(19),16-trien-7-yl]-carbamic acid tert-butyl ester [ No CAS ]
  • 30
  • [ 77611-37-1 ]
  • [(7S,10S,13S)-13-(2-Diazo-acetyl)-10-isopropyl-8,11-dioxo-2-oxa-9,12-diaza-bicyclo[13.2.2]nonadeca-1(18),15(19),16-trien-7-yl]-carbamic acid tert-butyl ester [ No CAS ]
  • 31
  • [ 77611-37-1 ]
  • ((10S)-butyl-(13S)-[(R)-oxiranyl]-8,11-dioxo-2-oxa-9,12-diaza-bicyclo[13.2.2]nonadeca-1(18),15(19),16-trien-(7S)-yl)-carbamic acid tert-butyl ester [ No CAS ]
  • 32
  • [ 77611-37-1 ]
  • (7S,10S,13S)-7-tert-Butoxycarbonylamino-10-butyl-8,11-dioxo-2-oxa-9,12-diaza-bicyclo[13.2.2]nonadeca-1(18),15(19),16-triene-13-carboxylic acid methyl ester [ No CAS ]
  • 33
  • [ 77611-37-1 ]
  • [(7S,10S,13S)-13-((S)-2-Bromo-1-hydroxy-ethyl)-10-isopropyl-8,11-dioxo-2-oxa-9,12-diaza-bicyclo[13.2.2]nonadeca-1(18),15(19),16-trien-7-yl]-carbamic acid tert-butyl ester [ No CAS ]
  • 34
  • [ 77611-37-1 ]
  • [(7S,10S,13S)-13-((R)-2-Bromo-1-hydroxy-ethyl)-10-isopropyl-8,11-dioxo-2-oxa-9,12-diaza-bicyclo[13.2.2]nonadeca-1(18),15(19),16-trien-7-yl]-carbamic acid tert-butyl ester [ No CAS ]
  • 35
  • [ 77611-37-1 ]
  • (S)-2-[(S)-2-((S)-6-Bromo-2-tert-butoxycarbonylamino-hexanoylamino)-3-methyl-butyrylamino]-3-(4-hydroxy-phenyl)-propionic acid methyl ester [ No CAS ]
  • 36
  • [ 77611-37-1 ]
  • (7S,10S,13S)-7-tert-Butoxycarbonylamino-8,11-dioxo-10-propoxymethyl-2-oxa-9,12-diaza-bicyclo[13.2.2]nonadeca-1(18),15(19),16-triene-13-carboxylic acid methyl ester [ No CAS ]
  • 37
  • [ 77611-37-1 ]
  • ((13S)-[(R)-oxiranyl]-8,11-dioxo-(10S)-propoxymethyl-2-oxa-9,12-diaza-bicyclo[13.2.2]nonadeca-1(18),15(19),16-trien-(7S)-yl)-carbamic acid tert-butyl ester [ No CAS ]
  • 38
  • [ 77611-37-1 ]
  • [(7S,10S,13S)-10-Butyl-13-(2-diazo-acetyl)-8,11-dioxo-2-oxa-9,12-diaza-bicyclo[13.2.2]nonadeca-1(18),15(19),16-trien-7-yl]-carbamic acid tert-butyl ester [ No CAS ]
  • 39
  • [ 77611-37-1 ]
  • [ 398526-22-2 ]
  • 40
  • [ 77611-37-1 ]
  • (S)-2-[(S)-2-((S)-2-tert-Butoxycarbonylamino-6-iodo-hexanoylamino)-3-methyl-butyrylamino]-3-(4-hydroxy-phenyl)-propionic acid methyl ester [ No CAS ]
  • 41
  • [ 77611-37-1 ]
  • [ 398526-21-1 ]
  • 42
  • [ 77611-37-1 ]
  • [(7S,10S,13S)-13-(2-Bromo-acetyl)-10-butyl-8,11-dioxo-2-oxa-9,12-diaza-bicyclo[13.2.2]nonadeca-1(18),15(19),16-trien-7-yl]-carbamic acid tert-butyl ester [ No CAS ]
  • 43
  • [ 77611-37-1 ]
  • [(7S,10S,13S)-13-(2-Diazo-acetyl)-8,11-dioxo-10-propoxymethyl-2-oxa-9,12-diaza-bicyclo[13.2.2]nonadeca-1(18),15(19),16-trien-7-yl]-carbamic acid tert-butyl ester [ No CAS ]
  • 44
  • [ 77611-37-1 ]
  • [(7S,10S,13S)-13-(2-Bromo-acetyl)-8,11-dioxo-10-propoxymethyl-2-oxa-9,12-diaza-bicyclo[13.2.2]nonadeca-1(18),15(19),16-trien-7-yl]-carbamic acid tert-butyl ester [ No CAS ]
  • 45
  • [ 77611-37-1 ]
  • [(7S,10S,13S)-13-((S)-2-Bromo-1-hydroxy-ethyl)-8,11-dioxo-10-propoxymethyl-2-oxa-9,12-diaza-bicyclo[13.2.2]nonadeca-1(18),15(19),16-trien-7-yl]-carbamic acid tert-butyl ester [ No CAS ]
  • 46
  • [ 77611-37-1 ]
  • [(7S,10S,13S)-13-((R)-2-Bromo-1-hydroxy-ethyl)-8,11-dioxo-10-propoxymethyl-2-oxa-9,12-diaza-bicyclo[13.2.2]nonadeca-1(18),15(19),16-trien-7-yl]-carbamic acid tert-butyl ester [ No CAS ]
  • 47
  • [ 77611-37-1 ]
  • [(7S,10S,13S)-13-((S)-2-Bromo-1-hydroxy-ethyl)-10-butyl-8,11-dioxo-2-oxa-9,12-diaza-bicyclo[13.2.2]nonadeca-1(18),15(19),16-trien-7-yl]-carbamic acid tert-butyl ester [ No CAS ]
  • 48
  • [ 77611-37-1 ]
  • [(7S,10S,13S)-13-((R)-2-Bromo-1-hydroxy-ethyl)-10-butyl-8,11-dioxo-2-oxa-9,12-diaza-bicyclo[13.2.2]nonadeca-1(18),15(19),16-trien-7-yl]-carbamic acid tert-butyl ester [ No CAS ]
  • 49
  • [ 77611-37-1 ]
  • (S)-2-[(S)-2-((S)-2-tert-Butoxycarbonylamino-6-iodo-hexanoylamino)-hexanoylamino]-3-(4-hydroxy-phenyl)-propionic acid methyl ester [ No CAS ]
  • 50
  • [ 77611-37-1 ]
  • (S)-2-[(S)-2-((S)-6-Bromo-2-tert-butoxycarbonylamino-hexanoylamino)-hexanoylamino]-3-(4-hydroxy-phenyl)-propionic acid methyl ester [ No CAS ]
  • 51
  • [ 77611-37-1 ]
  • (S)-2-[(S)-2-((S)-6-Bromo-2-tert-butoxycarbonylamino-hexanoylamino)-3-propoxy-propionylamino]-3-(4-hydroxy-phenyl)-propionic acid methyl ester [ No CAS ]
  • 52
  • [ 77611-37-1 ]
  • (S)-2-[(S)-2-((S)-2-tert-Butoxycarbonylamino-6-iodo-hexanoylamino)-3-propoxy-propionylamino]-3-(4-hydroxy-phenyl)-propionic acid methyl ester [ No CAS ]
  • 53
  • [ 77611-37-1 ]
  • C30H45N3O9 [ No CAS ]
  • 54
  • [ 77611-37-1 ]
  • {(7S,10S,13S)-13-[(R)-1-Hydroxy-2-(3-methyl-butylamino)-ethyl]-10-isopropyl-8,11-dioxo-2-oxa-9,12-diaza-bicyclo[13.2.2]nonadeca-1(18),15(19),16-trien-7-yl}-carbamic acid tert-butyl ester [ No CAS ]
  • 55
  • [ 77611-37-1 ]
  • C31H47N3O9 [ No CAS ]
  • 56
  • [ 77611-37-1 ]
  • C31H47N3O10 [ No CAS ]
  • 57
  • [ 77611-37-1 ]
  • {(7S,10S,13S)-13-[(R)-1-Hydroxy-2-(3-methyl-butylamino)-ethyl]-8,11-dioxo-10-propoxymethyl-2-oxa-9,12-diaza-bicyclo[13.2.2]nonadeca-1(18),15(19),16-trien-7-yl}-carbamic acid tert-butyl ester [ No CAS ]
  • 58
  • [ 77611-37-1 ]
  • {(7S,10S,13S)-10-Butyl-13-[(R)-1-hydroxy-2-(3-methyl-butylamino)-ethyl]-8,11-dioxo-2-oxa-9,12-diaza-bicyclo[13.2.2]nonadeca-1(18),15(19),16-trien-7-yl}-carbamic acid tert-butyl ester [ No CAS ]
  • 59
  • [ 77611-37-1 ]
  • [ 398526-26-6 ]
  • 60
  • [ 77611-37-1 ]
  • [ 398526-29-9 ]
  • 61
  • [ 77611-37-1 ]
  • 4-amino-N-[2-((7S)-amino-8,11-dioxo-(10S)-propoxymethyl-2-oxa-9,12-diaza-bicyclo[13.2.2]nonadeca-1(18),15(19),16-trien-(13S)-yl)-(2R)-hydroxy-ethyl]-N-(3-methyl-butyl)benzenesulfonamide [ No CAS ]
  • 62
  • [ 77611-37-1 ]
  • N-{4-[[(R)-2-((7S,10S,13S)-7-Amino-10-butyl-8,11-dioxo-2-oxa-9,12-diaza-bicyclo[13.2.2]nonadeca-1(18),15(19),16-trien-13-yl)-2-hydroxy-ethyl]-(3-methyl-butyl)-sulfamoyl]-phenyl}-acetamide [ No CAS ]
  • 63
  • [ 77611-37-1 ]
  • N-((13S)-{2-[(4-amino-benzenesulfonyl)-(3-methylbutyl)-amino]-(1R)-hydroxy-ethyl}-(10S)-butyl-8,11-dioxo-2-oxa-9,12-diaza-bicyclo[13.2.2]nonadeca-1(18),15(19),16-trien-(7S)-yl)acetamide [ No CAS ]
  • 64
  • [ 77611-37-1 ]
  • (S)-2-Amino-N-((7S,10S,13S)-13-{(R)-2-[(4-amino-benzenesulfonyl)-(3-methyl-butyl)-amino]-1-hydroxy-ethyl}-10-isopropyl-8,11-dioxo-2-oxa-9,12-diaza-bicyclo[13.2.2]nonadeca-1(18),15(19),16-trien-7-yl)-3-hydroxy-propionamide [ No CAS ]
  • 65
  • [ 77611-37-1 ]
  • [ 398526-27-7 ]
  • 66
  • [ 77611-37-1 ]
  • pentanoic acid (13(S)-{2-[(4-amino-benzenesulfonyl)-(3-methyl-butyl)amino]-(1R)-hydroxy-ethyl}-(10S)-butyl-8,11-dioxo-2-oxa-9,12-diaza-bicyclo[13.2.2]nonadeca-1(18),15(19),16-trien-(7S)-yl)amide [ No CAS ]
  • 67
  • [ 77611-37-1 ]
  • [ 398526-30-2 ]
  • 68
  • [ 77611-37-1 ]
  • (S)-2-Acetylamino-N-((7S,10S,13S)-13-{(R)-2-[(4-amino-benzenesulfonyl)-(3-methyl-butyl)-amino]-1-hydroxy-ethyl}-10-isopropyl-8,11-dioxo-2-oxa-9,12-diaza-bicyclo[13.2.2]nonadeca-1(18),15(19),16-trien-7-yl)-3-hydroxy-propionamide [ No CAS ]
  • 69
  • [ 77611-37-1 ]
  • (2S)-amino-N-((13S)-{2-[(4-amino-benzenesulfonyl)-(3-methylbutyl)-amino]-(1R)-hydroxy-ethyl}-(10S)-butyl-8,11-dioxo-2-oxa-9,12-diaza-bicyclo[13.2.2]nonadeca-1(18),15(19),16-trien-(7S)-yl)-3-hydroxy-propionamide [ No CAS ]
  • 70
  • [ 77611-37-1 ]
  • [ 398526-36-8 ]
  • 71
  • [ 77611-37-1 ]
  • [(S)-1-((7S,10S,13S)-13-{(R)-2-[(4-Amino-benzenesulfonyl)-(3-methyl-butyl)-amino]-1-hydroxy-ethyl}-10-isopropyl-8,11-dioxo-2-oxa-9,12-diaza-bicyclo[13.2.2]nonadeca-1(18),15(19),16-trien-7-ylcarbamoyl)-2-hydroxy-ethyl]-carbamic acid tert-butyl ester [ No CAS ]
  • 72
  • [ 77611-37-1 ]
  • [ 398526-33-5 ]
  • 73
  • [ 77611-37-1 ]
  • [ 200405-52-3 ]
  • 74
  • [ 77611-37-1 ]
  • (+)-deoxypyridinoline [ No CAS ]
  • 75
  • [ 77611-37-1 ]
  • [ 791044-51-4 ]
  • 76
  • [ 77611-37-1 ]
  • [ 106-95-6 ]
  • [ 243130-07-6 ]
YieldReaction ConditionsOperation in experiment
92% With sodium hydrogencarbonate; In N,N-dimethyl-formamide; at 0 - 20℃; for 22h; (S)-Allyl 6-bromo-2-(tert-butoxycarbonylamino)hexanoate (185)At 0 C., allyl bromide (3.9 mL, 45 mmol) was slowly added to a soln of <strong>[77611-37-1]Boc-L-6-hydroxynorleucine</strong> (183; 8.55 g, 34.6 mmol) and NaHCO3 (7.26 g, 86.4 mmol) in DMF (120 mL). The mixture was stirred for 4 h at 0 C. to rt, followed by the addition of more NaHCO3 (7.26 g, 86.4 mmol) and allyl bromide (3.9 mL, 45 mmol). Stirring was continued for 18 h. The mixture was distributed between EtOAc and aq. NaCl soln. The organic phase was separated, washed (diluted aq. NaCl soln, H2O, sat. aq. NaCl soln), dried (Na2SO4), filtered and concentrated. FC (hexane/EtOAc 2:1 to 1:2) afforded 184 (9.17 g, 92%). The alcohol 184 was converted into the bromide 185 following the procedure described for the synthesis of (2S)-2[(benzyloxycarbonyl)amino]-6-bromohexanoic acid methyl ester (R. Bambal and R. P. Hanzlik, J. Org. Chem. 1994, 59, 729-732). Data of 185: C14H24BrNO4 (350.2). LC-MS (method 10c): Rt=2.30 (91), 352/350 ([M+H]+). 1H-NMR (DMSO-d6): 7.29 (d, J=7.8, 1H), 5.89 (m, 1H), 5.32 (dd, J=1.6, 17.2, 1H), 5.21 (dd, J=1.3, 10.5, 1H), 4.59-4.55 (m, 2H), 3.94 (m, 1H), 3.51 (t, J=6.6, 2H), 1.83-1.57 (2 m, 4H), 1.47-1.33 (m, 2H), 1.38 (s, 9H).
  • 77
  • [ 24424-99-5 ]
  • [ 77611-37-1 ]
  • 78
  • [ 77302-72-8 ]
  • [ 77611-37-1 ]
YieldReaction ConditionsOperation in experiment
67% With sodium tetrahydroborate; iodine; In tetrahydrofuran; at 0 - 20℃; for 1.16667h; Example 3; Preparation of L-N-tert-butoxycarbonyl-epsilon-hydroxynorleucine (1); [0029] 500 mg of L-N-tert-butoxycarbonyl-homoglutamic acid and 217 mg of sodium borohydride were dissolved in 20 ml of tetrahydrofuran with stirring. To the mixture, 632 mg of iodine in 5 ml tetrahydrofuran solution was added dropwise for 10 minutes while cooling the mixture on ice, and stirring was continued for 1 hour at room temperature. 5 ml of methanol was carefully added to the reaction mixture while cooling the mixture on ice, and stirring was continued for 10 minutes to degrade an excess amount of reducing agent. After removing the solvent under reduced pressure, 15 ml of ethyl acetate was added to the residue, and extracted twice with 15 ml and 5 ml of water the first and second times, respectively. The aqueous phases obtained were combined, and 8 g of sodium chloride was added thereto for saturation. After adjusting to pH 3 with 1 moll of hydrochloric acid, the solution was extracted twice with 20 ml and 10 ml of ethyl acetate the first and second times, respectively. After the organic phases obtained were combined and dried with anhydrous sodium sulfate, they were concentrated under reduced pressure and dried under a vacuum to give 317 mg of a crude product of the compound of interest as a colorless syrup (with a crude yield of 67%). [0030] A portion (184 mg) of the resulting crude product was dissolved in 2.5 ml of 20% methanol and adsorbed to 2 ml of Diaion PA308 ion-exchange resin (manufactured by Mitsubishi Chemical Corporation). After washing with water, it was eluted with 15 ml of 0.1 mol/l hydrochloric acid. The eluate was extracted with ethyl acetate. It was concentrated to give 64 mg of a purified product of the compound of interest. When the specific optical rotation of the purified product obtained was measured, the value corresponded to the value described in the literature (J. Am. Chem. Soc., 104, 3096 (1982)), confirming that configuration had been maintained.
53% With sodium tetrahydroborate; boron trifluoride diethyl etherate; In tetrahydrofuran; at 0℃; for 2h; Example 4; Preparation of L-N-tert-butoxycarbonyl-epsilon-hydroxynorleucine (2); [0031] 21.7 mg of sodium borohydride and 72.8 mul (0.575 mmol) of boron trifluoride ether complex were sequentially added to 100 mg of L-N-tert-butoxycarbonyl-homoglutamic acid in 1 ml of tetrahydrofuran solution while cooling the solution on ice. After continuing the reaction for 2 hours at the same temperature, 30 ml of water was added to the reaction mixture. Furthermore, the mixture was adjusted to pH 4 with 0.1 mol/l of hydrochloric acid and stirring was continued for 10 minutes. Subsequently, after adjusting the pH to 9 with 5 mol/l of sodium hydroxide solution, the solution was washed with ethyl acetate. The aqueous phase was adjusted to pH 3 with 1 mol/l of hydrochloric acid, and was extracted twice with 30 ml of ethyl acetate both times. The ethyl acetate phase obtained was washed with 0.001 mol/l of hydrochloric acid, and then dried with anhydrous sodium sulfate. The solvent was removed by concentration under reduced pressure to obtain 51.1 mg of a crude product containing the compound of interest as a main component (with a crude yield of 53%).
YieldReaction ConditionsOperation in experiment
93% D. (L)-N-Boc-6-hydroxynorleucine (9) To a solution of (L)-6-hydroxynorleucine (16) (12.0 g, 81.5 mmol) and triethylamine (11.4 mL, 81.8 mmol) in a tetrahydrofuran (THF)-water mixture (1:1, 420 mL) was added a solution of di-tert-butyl dicarbonate (BOC)2 O (21.3 g, 97.6 mmol) in THF (30 mL). After stirring overnight at room temperature, the volume was reduced one-half under reduced pressure. To the mixture was added 1 N NaOH (100 mL) and was washed with EtOAc (3*100 mL). The aqueous layer was acidified to a pH 3 with citric acid (19.4 g, 101 mmol) and extracted with EtOAc (3*100 mL). The organic layer was dried (Na2 SO4), filtered and the solvent removed under reduced pressure to provide a clear oil which crystallizes on standing in cooled storage to afford a white solid (18.7 g, 93%). The material was dissolved in EtOAc (350 mL) with heating (bath, 65 C.) and hexane (300 mL) was added gradually to the warm solution. The solution was allowed to stand overnight at room temperature and the white crystalline solids identified as (L)-N-Boc-6-hydroxynorleucine (9) were filtered and washed with EtOAc-hexane (1:1, 4*30 mL) (16.1 g, 80%): mp 113-115 C. (lit.1 mp 112-113 C.).
With lithium borohydride; In tetrahydrofuran; at 0 - 10℃; for 16h; General procedure: To a solution of LiBEl4 (30 g, 136 mol) in THF (500 mL) was added dropwise a solution of compound 26A (75 g, 272.43 mmol) in THF (150 mL) at 0 C. After addition, the reaction mixture was stirred at 0 C for I h, then warmed to 10 C and stirred for 16 hrs. Then 14eOH (300 mU) was added into the reaction mixture slowly and stirred for 30 mm followed by added NH4C1 (30 rnL) dropwise into the mixture slowly. The mixture was filtered, and the solid collected was washed with EtOAc (IL). The filtrate was concentrated and the residue was dissolved in water (800 mL) and EtOAc (800 mL). the mixture was separated and the aqueous was extracted with EtOAc (800 mL x 2). The combined extracts were dried over NaSO4 and concentrated in vacuo. The residue was diluted with MTBE and filtered to afford compound 26B (35 g, yield 58.6%) as white solid. 1H NMR (400MHz, CDCI3): 4.95 4.84 (m, IH), 3.75 3.50 (rn, 5H), 3.01 (hr. s., 1H, 2.49 (br. s., 1H), 1.67 141 (m. 13F).
  • 80
  • [ 75-09-2 ]
  • [ 77611-37-1 ]
  • [ 106-95-6 ]
  • [ 243130-07-6 ]
YieldReaction ConditionsOperation in experiment
89% With sodium hydrogencarbonate; In hexane; water; E. (L)-N-Boc-6-hydroxynorleucine allyl ester (10) A mixture of (L)-N-Boc-6-hydroxynorleucine (9) (28.5 g, 115 mmol), NaHCO3 (15.5 g, 184 mmol), tricaprylymethylammonium chloride (a phase transfer catalyst), (10.1 g, 25 mmol), allyl bromide (13 mL, 150 mmol), CH2 Cl2 (100 mL) and water (100 mL) was stirred vigorously at room temperature under N2. After 8 days the mixture was filtered and purified by flash chromatography (silica gel; EtOAc/hexane (1:9, v/v) and EtOAc/hexane (2:3, v/v)) to provide a light lime oil (29.6 g, 89%) determined to be (L)-N-Boc-6-hydroxynorleucine allyl ester (10): TLC (SiO2, EtOAc/hexane (1:1, v/v)) Rf =0.20; 1 H NMR (300 MHz, CDCl3) delta5.96-5.85 (m, 1 H), 5.38-5.24 (m, 2 H), 5.09 (br s,1 H), 4.72-4.58 (m, 2 H), 4.33 (br s, 1 H), 3.64 (t, J=6.3 Hz, 2 H), 1.96-1.20 (m, 15 H); mass spectrum (ESI), m/z 286 (M-H)-.
  • 81
  • [ 186581-53-3 ]
  • [ 77611-37-1 ]
  • [ 81505-49-9 ]
  • 82
  • [ 67-56-1 ]
  • [ 77611-37-1 ]
  • (S)-2-amino-6-hydroxyhexanoic acid methyl ester hydrochloride [ No CAS ]
  • 83
  • C14H16N2O [ No CAS ]
  • [ 77611-37-1 ]
  • [ 1229653-78-4 ]
  • 84
  • C15H18N2O [ No CAS ]
  • [ 77611-37-1 ]
  • [ 1229653-79-5 ]
  • 85
  • [ 16652-71-4 ]
  • [ 77611-37-1 ]
  • [ 1229653-66-0 ]
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