3-(((Benzyloxy)carbonyl)amino)-2,2-dimethylpropanoic acid → 3beta-[(2,2-Dimethyl)-3-(carbobenzyloxyamino)propionyloxy]-androstane-6,17-dione

HRID 1912752Notes

Reaction equation

HRID 1912752 reaction equation
[OH:1][C@H:2]1[CH2:19][CH2:18][C@@:17]2([CH3:20])[CH:4]([C:5](=[O:22])[CH2:6][C@@H:7]3[C@@H:16]2[CH2:15][CH2:14][C@@:12]2([CH3:13])[C@H:8]3[CH2:9][CH2:10][C:11]2=[O:21])[CH2:3]1.[CH2:23]([O:30][C:31]([NH:33][CH2:34][C:35]([CH3:40])([CH3:39])[C:36](O)=[O:37])=[O:32])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>>[CH3:39][C:35]([CH3:40])([CH2:34][NH:33][C:31]([O:30][CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)=[O:32])[C:36]([O:1][C@H:2]1[CH2:19][CH2:18][C@@:17]2([CH3:20])[CH:4]([C:5](=[O:22])[CH2:6][C@@H:7]3[C@@H:16]2[CH2:15][CH2:14][C@@:12]2([CH3:13])[C@H:8]3[CH2:9][CH2:10][C:11]2=[O:21])[CH2:3]1)=[O:37]

Participants

3

Reactant 2

HCID 145510103-(((Benzyloxy)carbonyl)amino)-2,2-dimethylpropanoic acidHCID 690126423beta-Hydroxy-5alpha-androstan-6,17-dione

Product 1

HCID 691334683beta-[(2,2-Dimethyl)-3-(carbobenzyloxyamino)propionyloxy]-androstane-6,17-dioneYield 92.3%

Procedure

Following the procedure described in Prepn. 68 and starting from 3β-hydroxyandrostane-6,17-dione (Prepn. 68, 0.50 g) and 3-(benzyloxycarbonylamino)-2,2-dimethylpropanoic acid (0.41 g), after purification by flash chromatography (SiO2; EtOAc:n-hexane 6:4) to give 3β-[(2,2-dimethyl)-3-(carbobenzyloxyamino)propionyloxy]-androstane-6,17-dione (0.81 g, 90%) was obtained. 1H-NMR (300 MHz, DMSO-d6, ppm from TMS): δ 7.34 (5H, m), 5.07 (2H, s), 7.01 (1H, m), 4.57 (1H, m), 2.50-1.10 (22H, m), 1.10 (6H, s), 0.78 (3H, s), 0.70 (3H, s).

Workup

  1. customafter purification by flash chromatography (SiO2; EtOAc:n-hexane 6:4)

Sources & evidence

ORD record
ord-4edb8c85d576443a843b679d4041b8b9
Source dataset
uspto-grants-2013_12
Patent number
US08609644B2

Reaction notes

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