181075-66-1|(S)-Methyl 3-amino-5-methylhexanoate| Ambeed

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Quality Control of [ 181075-66-1 ] Purity: 95% SDS Specification

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Product Details of [ 181075-66-1 ]

CAS No. :	181075-66-1
Formula :	C₈H₁₇NO₂
M.W :	159.23
SMILES Code :	CC(C)C[C@H](N)CC(OC)=O
MDL No. :	MFCD20921740
InChI Key :	LLLSCIXQSDYKEB-ZETCQYMHSA-N
Pubchem ID :	12989106

Safety of [ 181075-66-1 ]

GHS Pictogram:
Signal Word:	Danger
Hazard Statements:	H314
Precautionary Statements:	P280-P305+P351+P338-P310
Class:	8
UN#:	3259
Packing Group:	Ⅲ

Application In Synthesis of [ 181075-66-1 ]

* 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 [ 181075-66-1 ]

[ 181075-66-1 ] Synthesis Path-Downstream 1~38

1
[ 67919-80-6 ]
[ 181075-66-1 ]
[ 181075-67-2 ]

References: [1]Helvetica Chimica Acta,1996,vol. 79,p. 913 - 941.

2
methyl (S)-3-amino-5-methylhexanoate trifluoroacetic acid salt [ No CAS ]
[ 181075-66-1 ]

References: [1]Helvetica Chimica Acta,1996,vol. 79,p. 913 - 941.

3
[ 26164-26-1 ]
[ 181075-66-1 ]
(S)-3-((S)-2-Methoxy-2-phenyl-acetylamino)-5-methyl-hexanoic acid methyl ester [ No CAS ]

References: [1]Tetrahedron,2002,vol. 58,p. 7081 - 7091.

4
[ 279256-99-4 ]
[ 181075-66-1 ]

References: [1]Tetrahedron,2002,vol. 58,p. 7081 - 7091.

5
[ 180037-68-7 ]
[ 181075-66-1 ]

References: [1]Tetrahedron,2002,vol. 58,p. 7081 - 7091.

6
(S)-5-Methyl-3-(2-nitro-benzenesulfonylamino)-hexanoic acid [ No CAS ]
[ 181075-66-1 ]

References: [1]Tetrahedron,2002,vol. 58,p. 7081 - 7091.

7
[ 181075-66-1 ]
(4S,8S,12R)-4-Isobutyl-12-isopropyl-8-methyl-1,5,9-triaza-cyclododecane-2,6,10-trione [ No CAS ]

References: [1]Helvetica Chimica Acta,1996,vol. 79,p. 913 - 941.

8
[ 181075-66-1 ]
[ 181075-71-8 ]

References: [1]Helvetica Chimica Acta,1996,vol. 79,p. 913 - 941.

9
[ 181075-66-1 ]
[ 181075-63-8 ]

References: [1]Helvetica Chimica Acta,1996,vol. 79,p. 913 - 941.

10
[ 181075-66-1 ]
H-(S)-β³-HAla-(S)-β³-HLeu-OMe*trifluoroacetic acid [ No CAS ]

References: [1]Helvetica Chimica Acta,1996,vol. 79,p. 913 - 941.

11
[ 181075-66-1 ]
(4S,8S,12R,16S,20S,24R)-4,16-Diisobutyl-12,24-diisopropyl-8,20-dimethyl-1,5,9,13,17,21-hexaaza-cyclotetracosane-2,6,10,14,18,22-hexaone [ No CAS ]

References: [1]Helvetica Chimica Acta,1996,vol. 79,p. 913 - 941.

12
[ 181075-66-1 ]
[ 181075-76-3 ]

References: [1]Helvetica Chimica Acta,1996,vol. 79,p. 913 - 941.

13
[ 181075-66-1 ]
[ 181075-75-2 ]

References: [1]Helvetica Chimica Acta,1996,vol. 79,p. 913 - 941.

14
[ 181075-66-1 ]
H-(R)-β³-HVal-(S)-β³-HAla-(S)-β³-HLeu-OMe*TFA [ No CAS ]

References: [1]Helvetica Chimica Acta,1996,vol. 79,p. 913 - 941.

15
[ 181075-66-1 ]
[ 181075-72-9 ]

References: [1]Helvetica Chimica Acta,1996,vol. 79,p. 913 - 941.

16
[ 181075-66-1 ]
(S)-3-[(S)-3-((R)-3-Amino-4-methyl-pentanoylamino)-butyrylamino]-5-methyl-hexanoic acid pentafluorophenyl ester; compound with trifluoro-acetic acid [ No CAS ]

References: [1]Helvetica Chimica Acta,1996,vol. 79,p. 913 - 941.

17
[ 181075-66-1 ]
[ 181075-77-4 ]

References: [1]Helvetica Chimica Acta,1996,vol. 79,p. 913 - 941.

18
[ 181075-66-1 ]
H-(R)-β³-HVal-(S)-β³-HAla-(S)-β³-HLeu-(R)-β³-HVal-(S)-β³-HAla-(S)-β³-HLeu-OH*trifluoroacetic acid [ No CAS ]

References: [1]Helvetica Chimica Acta,1996,vol. 79,p. 913 - 941.

19
[ 181075-66-1 ]
H-(R)-β³-HVal-(S)-β³-HAla-(S)-β³-HLeu-(R)-β³-HVal-(S)-β³-HAla-(S)-β³-HLeu-OMe*TFA [ No CAS ]

References: [1]Helvetica Chimica Acta,1996,vol. 79,p. 913 - 941.

20
[ 181075-66-1 ]
(S)-3-[(S)-3-((R)-3-{(S)-3-[(S)-3-((R)-3-Amino-4-methyl-pentanoylamino)-butyrylamino]-5-methyl-hexanoylamino}-4-methyl-pentanoylamino)-butyrylamino]-5-methyl-hexanoic acid pentafluorophenyl ester; compound with trifluoro-acetic acid [ No CAS ]

References: [1]Helvetica Chimica Acta,1996,vol. 79,p. 913 - 941.

21
[ 181075-66-1 ]
[ 253178-33-5 ]
[ 1036275-17-8 ]

References: [1]Tetrahedron Asymmetry,2008,vol. 19,p. 847 - 856.

22
[ 181075-66-1 ]
[ 677300-31-1 ]
N-[(S)-1-methoxycarbonyl-4-methylpentyl]-(S)-2-cyano-2-fluoro-p-tolylacetamide [ No CAS ]

References: [1]Tetrahedron Asymmetry,2008,vol. 19,p. 847 - 856.

23
[ 38274-14-5 ]
[ 181075-66-1 ]
C₂₂H₂₇NO₂ [ No CAS ]

References: [1]Tetrahedron Letters,2008,vol. 49,p. 3475 - 3479.

24
[ 67-56-1 ]
[ 138165-75-0 ]
[ 181075-66-1 ]

References: [1]Journal of the American Chemical Society,2009,vol. 131,p. 14521 - 14525.

25
[ 181075-66-1 ]
[ 357953-51-6 ]
[ 1190881-05-0 ]

References: [1]Journal of the American Chemical Society,2009,vol. 131,p. 14521 - 14525.

26
[ 15761-39-4 ]
[ 181075-66-1 ]
[ 1200953-81-6 ]

References: [1]Journal of Organic Chemistry,2009,vol. 74,p. 9562 - 9565.

27
[ 1228754-04-8 ]
[ 181075-66-1 ]
[ 1228754-17-3 ]

References: [1]Synlett,2010,p. 715 - 720.

28
[ 19099-93-5 ]
[ 181075-66-1 ]
C₂₁H₃₀N₂O₄ [ No CAS ]

References: [1]Angewandte Chemie - International Edition,2014,vol. 53,p. 3594 - 3598.
Angew. Chem.,2014,vol. 126,p. 3668 - 3672,5.

29
[ 67-56-1 ]
[ 172695-24-8 ]
[ 181075-66-1 ]

References: [1]Angewandte Chemie - International Edition,2014,vol. 53,p. 3594 - 3598.
Angew. Chem.,2014,vol. 126,p. 3668 - 3672,5.

30
[ 13139-15-6 ]
[ 181075-66-1 ]

References: [1]Angewandte Chemie - International Edition,2014,vol. 53,p. 3594 - 3598.
Angew. Chem.,2014,vol. 126,p. 3668 - 3672,5.

31
[ 66866-44-2 ]
[ 181075-66-1 ]

References: [1]Angewandte Chemie - International Edition,2014,vol. 53,p. 3594 - 3598.
Angew. Chem.,2014,vol. 126,p. 3668 - 3672,5.

32
[ 82010-31-9 ]
[ 181075-66-1 ]

References: [1]Angewandte Chemie - International Edition,2014,vol. 53,p. 3594 - 3598.
Angew. Chem.,2014,vol. 126,p. 3668 - 3672,5.

33
[ 109687-65-2 ]
[ 181075-66-1 ]

References: [1]Angewandte Chemie - International Edition,2014,vol. 53,p. 3594 - 3598.
Angew. Chem.,2014,vol. 126,p. 3668 - 3672,5.

34
[ 181075-66-1 ]
C₂₃H₃₂N₂O₄ [ No CAS ]

References: [1]Angewandte Chemie - International Edition,2014,vol. 53,p. 3594 - 3598.
Angew. Chem.,2014,vol. 126,p. 3668 - 3672,5.

35
[ 181075-66-1 ]
(S)-6-isobutyl-4-methoxy-1-(piperidin-4-yl)-5,6-dihydropyridin-2(1H)-one [ No CAS ]

References: [1]Angewandte Chemie - International Edition,2014,vol. 53,p. 3594 - 3598.
Angew. Chem.,2014,vol. 126,p. 3668 - 3672,5.

36
[ 181075-66-1 ]
(S)-6-isobutyl-1-(1-((S)-2-isobutyl-6-oxo-1,2,3,6-tetrahydropyridin-4-yl)piperidin-4-yl)-4-methoxy-5,6-dihydropyridin-2(1H)-one [ No CAS ]

References: [1]Angewandte Chemie - International Edition,2014,vol. 53,p. 3594 - 3598.
Angew. Chem.,2014,vol. 126,p. 3668 - 3672,5.

37
[ 181075-66-1 ]
C₂₁H₃₂N₂O₄ [ No CAS ]

References: [1]Angewandte Chemie - International Edition,2014,vol. 53,p. 3594 - 3598.
Angew. Chem.,2014,vol. 126,p. 3668 - 3672,5.

38
[ 1586791-15-2 ]
[ 181075-66-1 ]
methyl (S)-5-methyl-3-{(1-(pentan-3-yl)-2-(thiophen-2-ylmethyl)-1H-benzo[d]imidazole-5-carboxamido)}hexanoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
58%		To a well-stirred solution of carboxylic acid 8 (500 mg, 1.5 mmol) in dry DMF (10 mL) at 0 C under nitrogen, HOBt(310 mg, 2.3 mmol), EDC (450 mg, 2.89 mmol), and DIEA (0.60 mL, 452 mg, 3.9 mmol) were added consecutively. After 15 min stirring at 0 C, a solution of methyl (S)-3-amino-5-methylhexanoate (850 mg, 5.3 mmol) and DIEA (0.6 mL, 452mg, 3.9 mmol) in dry DMF (2 mL) was added. The reaction mixture was stirred at ambient temperature for 3 days and poured into water (125 mL). The solution was acidified to pH 3 by the addition of 2.0 M aqueous HCl and extracted with ethyl acetate (2 x 250 mL). The combined organic phase was washed with saturated sodium bicarbonate (2 x 200 mL) and brine (200 mL), dried over sodium sulfate, filtered, and evaporated. Purification of the residue by FC on Florisil (20% ethyl acetate in hexane) yielded 420 mg (58%) of the title product 9 as a pale brown oil, Rf = 0.36 (ethyl acetate/toluene, 1:1); [α]D25 = 23.7 (c = 0.002, CHCl3). 1H NMR (400 MHz, C6D6): = 8.58 (s, 1 H, 4-HBZM), 8.16 (d, J = 8.4 Hz, 1 H, 6-HBZM), 7.17-7.13 (m, 2 H, NH + 7-HBZM), 6.78 (d, J = 5.2 Hz, 1 H, 5-HTh), 6.70 (d, J = 2.0 Hz, 1 H, 3-HTh), 6.66-6.64 (m, 1H, 4-HTh), 4.87-4.81 (m, 1 H, CONHCH), 4.24 (s, 2 H,CBZMCH2CTh), 3.76-3.70 (m, 1 H, NBZMCH), 3.32 (s, 3 H,CH3O), 2.54-2.45 (m, 2 H, CH3O2CCH2), 1.74-1.66 (m, 1 H,CH(CH3)2), 1.63-1.54 [m, 3 H, CHaHbCH(CH3)2 + CH2CH3],1.41-1.31 (m, 2 H, CH2CH3), 1.28-1.21 [m, 1 H,CHaHbCH(CH3)2], 0.95 [d, J = 6.4 Hz, 3 H, CH(CH3)CH3],0.84 [d, J = 6.4 Hz, 3 H, CH(CH3)CH3], 0.34 (t, J = 7.2 Hz, 6H, 2 CH2CH3) ppm. 13C NMR (100 MHz, C6D6): = 172.4(CO2CH3), 167.0 (CONH), 154.7 (2-CBZM), 143.7 (9-CBZM),139.3 (2-CTh), 136.0 (8-CBZM), 129.7 (5-CBZM), 127.1 (4-HCTh), 126.5 (3-HCTh), 124.9 (5-HCTh), 122.8 (6-HCBZM),119.1 (4-HCBZM), 111.9 (7-HCBZM), 60.7 (NBZMCH), 51.2(CH3O), 45.2 (CONHCH), 43.9 [CH2CH(CH3)2], 39.8(CH3O2CCH2), 29.6 (CThCH2), 26.7 (2 CH2CH3), 25.5[CH(CH3)2], 23.3 [CH(CH3)CH3], 22.3 [CH(CH3)CH3], 10.8(2 CH2CH3) ppm. HRMS (ESI): calcd. for C26H36N3O3S+[M +H+]: 470.2472; found: 470.2479.

References: [1]Medicinal Chemistry,2018,vol. 14,p. 688 - 694.

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H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

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CAS No.: 181075-66-1

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CAS No.: 181075-66-1

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[ 181075-66-1 ] Synthesis Path-Downstream 1~38

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