Dicyclohexylcarbodiimide → HCID 69134050, compound

HRID 1912730Notes

Reaction equation

HRID 1912730 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.[CH:23]1[C:35]2[CH:34]([CH2:36][O:37][C:38]([NH:40][CH2:41][C:42](O)=[O:43])=[O:39])[C:33]3[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=3)[C:27]=2[CH:26]=[CH:25][CH:24]=1.C1(N=C=NC2CCCCC2)CCCCC1>C1COCC1.CN(C)C1C=CN=CC=1>[CH:32]1[C:33]2[CH:34]([CH2:36][O:37][C:38]([NH:40][CH2:41][C:42]([O:1][C@H:2]3[CH2:19][CH2:18][C@@:17]4([CH3:20])[CH:4]([C:5](=[O:22])[CH2:6][C@@H:7]5[C@@H:16]4[CH2:15][CH2:14][C@@:12]4([CH3:13])[C@H:8]5[CH2:9][CH2:10][C:11]4=[O:21])[CH2:3]3)=[O:43])=[O:39])[C:35]3[C:27](=[CH:26][CH:25]=[CH:24][CH:23]=3)[C:28]=2[CH:29]=[CH:30][CH:31]=1

Participants

6

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 93124Fmoc-Gly-OHHCID 690126423beta-Hydroxy-5alpha-androstan-6,17-dione

Product 1

HCID 69134050HCID 69134050, compoundYield 95%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3β-hydroxyandrostane-6,17-dione (0.40 g) in THF (8 mL), N-(9-fluorenylmethoxycarbonyl)glycine (0.43 g), N,N′-dicyclohexylcarbodiimide (0.32 g) and 4-dimethylaminopyridine (16 mg) were added and the reaction mixture was stirred at room temperature for 1 h. After evaporation to dryness, the residue was purified by flash chromatography (SiO2; EtOAc:n-hexane 6:4) to give 3β-{2-[N-(9-fluorenylmethoxycarbonyl)]aminoacetoxy}androstane-6,17-dione (0.73 mg, 95%). 1H-NMR (300 MHz, acetone, ppm from TMS): δ 7.93-7.30 (8H, m), 6.86 (1H, t), 4.71 (1H, m), 4.40-4.20 (3H, m), 3.91 (2H, d), 2.55-1.25 (20H, m), 0.87 (3H, s), 0.78 (3H, s).

Workup

  1. customAfter evaporation to dryness
  2. customthe residue was purified by flash chromatography (SiO2; EtOAc:n-hexane 6:4)

Sources & evidence

ORD record
ord-dcca87ce6b0f4daf970c77ae27dc7cb1
Source dataset
uspto-grants-2013_12
Patent number
US08609644B2

Reaction notes

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