[ CAS No. 116821-47-7 ] {[proInfo.proName]}

Name: 116821-47-7|Fmoc-GABA-OH|97%
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Quality Control of [ 116821-47-7 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 116821-47-7 ]

Product Details of [ 116821-47-7 ]

CAS No. :	116821-47-7	MDL No. :	MFCD00144889
Formula :	C₁₉H₁₉NO₄	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	ACUIFAAXWDLLTR-UHFFFAOYSA-N
M.W :	325.36	Pubchem ID :	2756086
Synonyms :	Fmoc-GABA-OH

Calculated chemistry of [ 116821-47-7 ]

Physicochemical Properties

Num. heavy atoms :	24
Num. arom. heavy atoms :	12
Fraction Csp3 :	0.26
Num. rotatable bonds :	8
Num. H-bond acceptors :	4.0
Num. H-bond donors :	2.0
Molar Refractivity :	89.98
TPSA :	75.63 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	Yes
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	Yes
CYP2C9 inhibitor :	Yes
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.22 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.65
Log Po/w (XLOGP3) :	2.91
Log Po/w (WLOGP) :	3.39
Log Po/w (MLOGP) :	2.55
Log Po/w (SILICOS-IT) :	3.09
Consensus Log Po/w :	2.92

Druglikeness

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

Water Solubility

Log S (ESOL) :	-3.53
Solubility :	0.0955 mg/ml ; 0.000293 mol/l
Class :	Soluble
Log S (Ali) :	-4.16
Solubility :	0.0226 mg/ml ; 0.0000693 mol/l
Class :	Moderately soluble
Log S (SILICOS-IT) :	-5.67
Solubility :	0.000704 mg/ml ; 0.00000216 mol/l
Class :	Moderately soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	3.35

Safety of [ 116821-47-7 ]

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 [ 116821-47-7 ]

* 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.

Upstream synthesis route of [ 116821-47-7 ]
Downstream synthetic route of [ 116821-47-7 ]

[ 116821-47-7 ] Synthesis Path-Upstream 1~4

1
[ 82911-69-1 ]
[ 56-12-2 ]
[ 116821-47-7 ]

Yield	Reaction Conditions	Operation in experiment
73%	With sodium hydrogencarbonate In water; acetonitrile at 20℃; for 3 h;	To a solution of GAB A (2.00 g, 19.4 mmol, in 14 mL 10percent NaHC0₃), Fmoc-OSu (4 g, 11.7 mmol, in 40 mL ACN) was added drop-wise over a period of 2 h at room temperature. The mixture was allowed to stir at room temperature for an additional hour. ACN was removed under reduced pressure and the aqueous layer acidified to pH 1 with 10percent HCl. The precipitate was washed with two 20 mL portions of water, 20 mL ethyl acetate and dried under reduced pressure. Fmoc-GABA was obtained as a white solid in 73percent yield (2.8 g). [65] NMR (DMSO-d6, 400 MHz): δ 7.89 (d, 2H, J = 7.4 Hz), 7.44 (d, 2H, J = 7.2 Hz), 7.42 (t, 2H, J = 7.5 Hz), 7.35 (s, 1H), 7.33 (t, 2H, J = 7.0 Hz), 4.30 (d, 2H, J = 7 Hz), 4.21 (t, 1H, J = 6.7 Hz), 3.01 ( q, 2H, J = 5.6 Hz ), 2.20 ( t, 2H, J = 7.3 Hz ), 1.63 (q, 2H, J = 7.1 Hz); ¹³C NMR (DMSO-d6, 100 MHz): δ 142.6, 139.4, 137.4, 128.9, 127.2, 124.2, 121.3, 120.0, 109.6, 77.5, 61.8, 51.1, 31.6; MS (ESI+): m/z (intensity), 325.8 ([M+H]+, 100percent).

Reference： [1] Chemical Biology and Drug Design, 2015, vol. 86, # 4, p. 837 - 848
[2] Patent: WO2018/144880, 2018, A1, . Location in patent: Paragraph 64-65

2
[ 851713-93-4 ]
[ 116821-47-7 ]

Reference： [1] Organic Letters, 2005, vol. 7, # 8, p. 1473 - 1475

3
[ 28920-43-6 ]
[ 56-12-2 ]
[ 116821-47-7 ]

Reference： [1] Chemistry - A European Journal, 1998, vol. 4, # 3, p. 425 - 433
[2] Tetrahedron Letters, 1998, vol. 39, # 28, p. 5117 - 5120
[3] Bioorganic Chemistry, 1996, vol. 24, # 1, p. 50 - 58
[4] Tetrahedron Letters, 2004, vol. 45, # 19, p. 3703 - 3706
[5] Patent: US2003/143591, 2003, A1,
[6] Russian Journal of General Chemistry, 2010, vol. 80, # 12, p. 2572 - 2589

4
[ 869541-06-0 ]
[ 116821-47-7 ]

Reference： [1] Journal of Organic Chemistry, 2005, vol. 70, # 22, p. 8730 - 8733

[ 116821-47-7 ] Synthesis Path-Downstream 1~69

1
[ 112883-29-1 ]
[ 135273-01-7 ]
[ 116821-47-7 ]
(4R,12R)-12-[(S)-2-Amino-3-(4-hydroxy-phenyl)-propionylamino]-6,11-dioxo-1,2-dithia-5,10-diaza-cyclotridecane-4-carboxylic acid [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,1997,vol. 40,p. 3359 - 3368

2
[ 20485-43-2 ]
[ 109-55-7 ]
[ 116821-47-7 ]
[ 195387-29-2 ]
Fmoc-β-alanine-Wang resin [ No CAS ]
C₅₉H₇₂N₂₀O₁₀ [ No CAS ]

Reference： [1]Organic Letters,2001,vol. 3,p. 1201 - 1203

3
[ 86060-98-2 ]
[ 86060-93-7 ]
[ 86060-92-6 ]
[ 116821-47-7 ]
[ 1027903-88-3 ]

Reference： [1]Journal of Medicinal Chemistry,2002,vol. 45,p. 670 - 675

4
[ 117-78-2 ]
[ 116821-47-7 ]
Arg^Pmc-Ual-Sar-Chi-Chi-Tal-Arg^Pmc-Rink amide MBHA resin [ No CAS ]
anthraquinone-2-carbonyl-γ-NH-butyryl-Arg-β-(uracyl-1-yl)-D-alanyl-Sar-[β-(1,2,3,4-tetrahydro-2,4-dioxoquinazolin-3-yl)-D-alanyl]2-β-(thymin-1-yl)-D-alanyl-Arg-NH2 [ No CAS ]

Reference： [1]Helvetica Chimica Acta,2003,vol. 86,p. 533 - 547

5
[ 3228-51-1 ]
[ 116821-47-7 ]
[ 115960-63-9 ]
2-cyanoethyl N,N,N',N'-tetraisopropylphosphordiamidite [ No CAS ]
C₄₆H₈₀ClN₇O₆P₂ [ No CAS ]

Reference： [1]Chemistry Letters,2003,vol. 32,p. 464 - 465

6
[ 44520-55-0 ]
[ 116821-47-7 ]
[ 115960-63-9 ]
2-cyanoethyl N,N,N',N'-tetraisopropylphosphordiamidite [ No CAS ]
C₄₆H₈₀ClN₇O₆P₂ [ No CAS ]

Reference： [1]Chemistry Letters,2003,vol. 32,p. 464 - 465

7
[ 68858-20-8 ]
[ 111061-56-4 ]
[ 116821-47-7 ]
[ 651311-59-0 ]
Fmoc-Arg(Pbf)-OH [ No CAS ]
4-[4-({(S)-2-[(S)-2-(4-Amino-butyrylamino)-3-hydroxy-propionylamino]-3-methyl-butyrylamino}-methyl)-phenylamino]-2-phenyl-quinoline-8-carboxylic acid ((S)-1-carbamoyl-4-guanidino-butyl)-amide [ No CAS ]

Reference： [1]Organic Letters,2004,vol. 6,p. 63 - 66

8
[ 3228-51-1 ]
[ 116821-47-7 ]
[ 142276-42-4 ]

Reference： [1]Tetrahedron Letters,2004,vol. 45,p. 3703 - 3706

9
[ 44520-55-0 ]
[ 116821-47-7 ]
[ 141925-88-4 ]

Reference： [1]Tetrahedron Letters,2004,vol. 45,p. 3703 - 3706

10
[ 1477-50-5 ]
[ 138775-07-2 ]
[ 116821-47-7 ]
4-{5-benzyloxycarbonylamino-2-[(1<i>H</i>-indole-2-carbonyl)-amino]-pentanoylamino}-butyric acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multistep reaction;

Reference： [1]Hattori, Kouji; Tanaka, Akira; Fujii, Naoaki; Takasugi, Hisashi; Tenda, Yoshiyuki; Tomita, Masayuki; Nakazato, Shoko; Nakano, Keiko; Kato, Yasuko; Kono, Yutaka; Murai, Hidetsugu; Sakane, Kazuo [Journal of Medicinal Chemistry, 2005, vol. 48, # 9, p. 3103 - 3106]

11
[ 108-24-7 ]
[ 117106-21-5 ]
[ 116821-47-7 ]
[ 195387-29-2 ]
[ 252206-28-3 ]
Fmoc-β-Ala-clear-acid resin [ No CAS ]
C₅₄H₇₄N₂₂O₁₁ [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2006,vol. 128,p. 8766 - 8776

12
[ 108-24-7 ]
[ 117106-21-5 ]
[ 116821-47-7 ]
[ 195387-29-2 ]
[ 252206-28-3 ]
Fmoc-β-Ala-clear-acid resin [ No CAS ]
C₅₄H₇₄N₂₂O₁₁ [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2006,vol. 128,p. 8766 - 8776

13
[ 881744-15-6 ]
[ 111061-56-4 ]
[ 116821-47-7 ]
Nα-(9-fluorenylmethyloxycarbonyl)-Nγ-2,2,4,6,7-pentamethyldihydrobenzofuran-5-sulfonyl-L-arginine [ No CAS ]
Fmoc-Val-OH [ No CAS ]
AbuSVQuinR [ No CAS ]

Reference： [1]Organic and Biomolecular Chemistry,2006,vol. 4,p. 639 - 645

14
[ 20485-43-2 ]
[ 116821-47-7 ]
[ 195387-29-2 ]
[ 252206-28-3 ]
Fmoc-β-alanine-Wang resin [ No CAS ]
N,N-dimethylaminopropylamine [ No CAS ]
C₅₈H₇₁N₂₁O₁₀ [ No CAS ]

Reference： [1]Organic Letters,2001,vol. 3,p. 1201 - 1203

15
[ 131570-56-4 ]
[ 116821-47-7 ]
N-α-(9-fluoromethoxycarbonyl)-L-4-tert-butoxycarbonylaminophenylalanine [ No CAS ]
[(S)-4-({Amino-[(E)-2,2,5,7,8-pentamethyl-chroman-6-sulfonylimino]-methyl}-amino)-1-hydroxymethyl-butyl]-carbamic acid 9H-fluoren-9-ylmethyl ester [ No CAS ]
1,4-dihydroquinoxaline-2,3-dione-6-carboxylic acid [ No CAS ]
2-fluoro-5-nitrobenzoic acid [ No CAS ]
2,3-Dioxo-1,2,3,4-tetrahydro-quinoxaline-6-carboxylic acid {3-[(7S,10S,13S)-13-amino-10-(4-amino-benzyl)-7-(3-guanidino-propyl)-9,12,16-trioxo-7,8,9,10,11,12,13,14,15,16-decahydro-6H-5-oxa-8,11,15-triaza-benzocyclotetradecen-2-ylcarbamoyl]-propyl}-amide [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2002,vol. 45,p. 3430 - 3439

16
C₂₇H₂₂N₂O₉S [ No CAS ]
[ 162558-25-0 ]
[ 116821-47-7 ]
Fmoc-D-Arg(Pmc)-OH [ No CAS ]
C₇₆H₁₂₀N₃₄O₁₇S [ No CAS ]

Reference： [1]Chemical and Pharmaceutical Bulletin,2008,vol. 56,p. 1515 - 1520
[2]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 5129 - 5132

17
C₂₇H₂₂N₂O₉S [ No CAS ]
[ 125238-99-5 ]
[ 116821-47-7 ]
Fmoc-D-Arg(Pmc)-OH [ No CAS ]
C₇₇H₁₂₂N₃₄O₁₇S [ No CAS ]

Reference： [1]Chemical and Pharmaceutical Bulletin,2008,vol. 56,p. 1515 - 1520
[2]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 5129 - 5132

18
(2E,4E)-5-{1-[(9H-fluoren-9-ylmethoxy)carbonyl]-4-piperidinyl}-2,4-pentadienoic acid [ No CAS ]
C₈H₁₁N₂Pol [ No CAS ]
[ 81196-09-0 ]
[ 116821-47-7 ]
[ 474453-47-9 ]
[ 583868-50-2 ]

Yield	Reaction Conditions	Operation in experiment
		In the above General Reaction Scheme, the following reaction sequence was well suited for the solid-phase synthesis. Thus, when the resin-bound amine, prepared by reacting H2N-A-NH2 with the commercially available Wang resin (1.0 mmol/g), was coupled to the requisite Fmoc-diene acid (a) (3.0 equiv) in the presence of BOP (3 equiv), HOBT (3 equiv) in DMF at room temperature for 4 h, the corresponding polymer-bound Fmoc-diene (b) was generated. Exposing this Fmoc-piperidine-diene unit to the Diels-Alder reaction conditions with the appropriate urazole (3 equiv) in the presence of [bis(trifluoroacetoxy)iodo]benzene (3 equiv) for 3 h at room temperature, efficiently yielded the resin-bound bicyclic compound (c). Deprotection of the Fmoc with 25% piperidine/DMF followed by coupling with Fmoc-acid linker (FmocHN-B-CO2H) employing the above coupling conditions provided the intermediate Fmoc-diene-linker. Final Fmoc removal and subsequent coupling with Boc-protected aromatic amino acids or an equivalent thereof (R1-CO2H), completes the chain length and sets the stage for the cleavage step. The desired inhibitor was then cleaved from the resin in concert with the Boc-protecting group on treatment with 95% TFA/H2O for 90 minutes. After this time, the supernatant was collected and combined with washes (2×1 mL 95% aq TFA). The residue obtained after evaporation of the solution was redissolved in either glacial acetic acid or 50:50 acetonitrile-water, frozen and lyophilized to provide the desired crude adduct (TFA salt).

Reference： [1]Patent: US2004/14763,2004,A1 .Location in patent: Page 15; 26

19
[ 446-31-1 ]
[ 116821-47-7 ]
[ 1053184-32-9 ]

Yield	Reaction Conditions	Operation in experiment
60%		4-Fmoc-amino buturic acid, 1.1 equiv. of HOBt, 1.1 equiv. of HBTU and 2 equiv. of DIPEA were solved in DMF/DCM (1/1 ) and stirred for 20 minutes at room temperature. 4-Amino-2-fluoro benzoic acid and 2 equiv. of DIPEA were added to the reaction mixture and stirred at room temperature over night. The solvent was removed under reduced pressure and the remaining residue is chromatographed (gradient: DCM/1- 3 % MeOH). Calculated: [M+H]+ = 463.5, found: [M+H]+ = 463.1. Yield: 60%.

Reference： [1]Patent: WO2008/104271,2008,A2 .Location in patent: Page/Page column 83-84

20
[ 511272-33-6 ]
[ 35661-39-3 ]
1-tert-butoxycarbonyl-N-[(9-fluorenyl)methoxycarbonyl]-D-tryptophan [ No CAS ]
[ 116821-47-7 ]
[ 1045712-56-8 ]

Yield	Reaction Conditions	Operation in experiment
	Multistep reaction.;

Reference： [1]Terracciano, Stefania; Bruno, Ines; D'Amico, Elisabetta; Bifulco, Giuseppe; Zampella, Angela; Sepe, Valentina; Smith, Charles D.; Riccio, Raffaele [Bioorganic and Medicinal Chemistry, 2008, vol. 16, # 13, p. 6580 - 6588]

21
[ 35661-39-3 ]
1-tert-butoxycarbonyl-N-[(9-fluorenyl)methoxycarbonyl]-D-tryptophan [ No CAS ]
[ 116821-47-7 ]
[ 220498-02-2 ]
[ 1045712-52-4 ]

Reference： [1]Bioorganic and Medicinal Chemistry,2008,vol. 16,p. 6580 - 6588

22
C₂₇H₂₂N₂O₉S [ No CAS ]
[ 125238-99-5 ]
[ 116821-47-7 ]
Fmoc-D-Arg(Pmc)-OH [ No CAS ]
C₂₃H₁₈N₂O₆S [ No CAS ]
C₅₄H₁₀₄N₃₂O₁₁ [ No CAS ]

Reference： [1]Chemical and Pharmaceutical Bulletin,2008,vol. 56,p. 1515 - 1520

23
C₂₇H₂₂N₂O₉S [ No CAS ]
[ 162558-25-0 ]
[ 116821-47-7 ]
Fmoc-D-Arg(Pmc)-OH [ No CAS ]
C₂₃H₁₈N₂O₆S [ No CAS ]
[ 1013427-97-8 ]

Reference： [1]Chemical and Pharmaceutical Bulletin,2008,vol. 56,p. 1515 - 1520

24
[ 3326-32-7 ]
[ 29022-11-5 ]
[ 35661-60-0 ]
[ 132327-80-1 ]
[ 111061-56-4 ]
[ 116821-47-7 ]
(S)-2-(((9H-fluoren-9-yl)methoxy)carbonylamino)-3-(4(bis(dimethylamino)phosphoryloxy)phenyl)propanoic acid [ No CAS ]
[ 1133164-00-7 ]

Reference： [1]Journal of Medicinal Chemistry,2009,vol. 52,p. 1612 - 1618

25
[ 3326-32-7 ]
[ 29022-11-5 ]
[ 35661-60-0 ]
[ 132327-80-1 ]
[ 111061-56-4 ]
[ 116821-47-7 ]
(S)-2-(((9H-fluoren-9-yl)methoxy)carbonylamino)-3-(4(bis(dimethylamino)phosphoryloxy)phenyl)propanoic acid [ No CAS ]
[ 1133163-69-5 ]

Reference： [1]Journal of Medicinal Chemistry,2009,vol. 52,p. 1612 - 1618

26
[ 88-14-2 ]
C₂₉H₃₇N₂O₃Pol [ No CAS ]
[ 29022-11-5 ]
[ 116821-47-7 ]
[ 188970-92-5 ]
C₅₄H₆₉N₈O₁₃Pol [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2010,vol. 49,p. 1492 - 1495

27
[ 6214-20-6 ]
[ 35661-40-6 ]
[ 77128-73-5 ]
[ 116821-47-7 ]
[ 1215027-79-4 ]

Reference： [1]Journal of Medicinal Chemistry,2010,vol. 53,p. 2354 - 2363

28
[ 3034-48-8 ]
[ 116821-47-7 ]
[ 50384-70-8 ]

Reference： [1]Russian Journal of General Chemistry,2010,vol. 80,p. 2572 - 2589

29
[ 31575-35-6 ]
[ 116821-47-7 ]
[ 852632-29-2 ]

Reference： [1]Russian Journal of General Chemistry,2010,vol. 80,p. 2572 - 2589

30
[ 1929-29-9 ]
[ 116821-47-7 ]
[ 359586-69-9 ]
[ 359586-64-4 ]
[ 1430116-35-0 ]

Reference： [1]Angewandte Chemie - International Edition,2013,vol. 52,p. 3712 - 3716
Angew. Chem.,2013,p. 3800 - 3804

31
[ 1929-29-9 ]
[ 116821-47-7 ]
[ 359586-69-9 ]
[ 1430116-34-9 ]

Reference： [1]Angewandte Chemie - International Edition,2013,vol. 52,p. 3712 - 3716
Angew. Chem.,2013,p. 3800 - 3804

32
[ 1929-29-9 ]
[ 116821-47-7 ]
[ 359586-64-4 ]
[ 1430116-35-0 ]

Reference： [1]Angewandte Chemie - International Edition,2013,vol. 52,p. 3712 - 3716
Angew. Chem.,2013,p. 3800 - 3804

33
[ 77128-73-5 ]
[ 135673-97-1 ]
[ 116821-47-7 ]
[ 1616762-30-1 ]