Gamma-Aminobutyric Acid → HCID 53308284, compound

HRID 879975Notes

Reaction equation

HRID 879975 reaction equation
[C:1](=[O:40])(OC1C=CC([N+]([O-])=O)=CC=1)[O:2][C@@H:3]1[CH2:19][C@@H:18]2[C@@:6]([CH3:29])([C@@H:7]3[C@@H:15]([CH2:16][CH2:17]2)[C@:14]2([OH:20])[C@@:10]([CH3:28])([C@@H:11]([C:21]4[CH:22]=[CH:23][C:24](=[O:27])[O:25][CH:26]=4)[CH2:12][CH2:13]2)[CH2:9][CH2:8]3)[CH2:5][CH2:4]1.[NH2:41][CH2:42][CH2:43][CH2:44][C:45]([OH:47])=[O:46].CCN(C(C)C)C(C)C>C(Cl)Cl.CN(C1C=CN=CC=1)C>[OH:20][C@:14]12[CH2:13][CH2:12][C@H:11]([C:21]3[CH:22]=[CH:23][C:24](=[O:27])[O:25][CH:26]=3)[C@@:10]1([CH3:28])[CH2:9][CH2:8][C@H:7]1[C@H:15]2[CH2:16][CH2:17][C@H:18]2[C@:6]1([CH3:29])[CH2:5][CH2:4][C@H:3]([O:2][C:1]([NH:41][CH2:42][CH2:43][CH2:44][C:45]([OH:47])=[O:46])=[O:40])[CH2:19]2

Participants

6

Reactant 3

HCID 119Gamma-Aminobutyric AcidHCID 81531DiisopropylethylamineHCID 58392955HCID 58392955, compound

Product 1

HCID 53308284HCID 53308284, compoundYield 53.9%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of (3S,5R,8R,9S,10S,13R,14S,17R)-14-hydroxy-10,13-dimethyl-17-(2-oxo-2H-pyran-5-yl)hexadecahydro-1H-cyclopenta[a]phenanthren-3-yl 4-nitrophenyl carbonate (20 mg, 0.036 mmol) in CH2Cl2 was added 4-aminobutanoic acid (37.1 mg, 0.36 mmol, 10 eq), DIEA (18.6 mg, 0.144 mmol, 4 eq) and DMAP (16.1 mg, 0.144 mmol, 4 eq). The resultant mixture was stirred at 40° C. for 16 h and then purified via preparative TLC to afford 4-(((3S,5R,8R,9S,10S,13R,14S,17R)-14-hydroxy-10,13-dimethyl-17-(2-oxo-2H-pyran-5-yl)hexadecahydro-1H-cyclopenta[a]phenanthren-3-yloxy)carbonylamino)butanoic acid (10 mg, 53.5%) as a white solid. LRMS (M−H+) m/z 514.4. 1H NMR (CD3OD, 400 MHz) δ 7.89 (dd, J=9.6, 2.4 Hz, 1H), 7.33 (m, 1H), 6.18 (d, J=9.6 Hz, 1H), 4.82 (m, 1H), 3.03 (m, 2H), 2.44-2.48 (m, 1H), 1.08-2.15 (m, 25H), 0.87 (s, 3H), 0.62 (s, 3H).

Workup

  1. custompurified via preparative TLC

Sources & evidence

ORD record
ord-62cf22ae7f1442daad43272019dab94d
Source dataset
uspto-grants-2015_03
Patent number
US08993550B2

Reaction notes

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