Potassium Hydroxide → HCID 69133356, compound

HRID 1912732Notes

Reaction equation

HRID 1912732 reaction equation
Cl.[NH2:2][C@H:3]1[CH2:20][CH2:19][C@@:18]2([CH3:21])[CH:5]([C:6](=[O:23])[CH2:7][C@@H:8]3[C@@H:17]2[CH2:16][CH2:15][C@@:13]2([CH3:14])[C@H:9]3[CH2:10][CH2:11][C:12]2=[O:22])[CH2:4]1.[OH-].[K+].[C:26]([O:30][C:31]([NH:33][CH2:34][CH2:35][CH2:36][C:37](O)=[O:38])=[O:32])([CH3:29])([CH3:28])[CH3:27].CCN=C=NCCCN(C)C>C(Cl)Cl.CN(C)C1C=CN=CC=1>[C:26]([O:30][C:31]([NH:33][CH2:34][CH2:35][CH2:36][C:37]([NH:2][C@H:3]1[CH2:20][CH2:19][C@@:18]2([CH3:21])[CH:5]([C:6](=[O:23])[CH2:7][C@@H:8]3[C@@H:17]2[CH2:16][CH2:15][C@@:13]2([CH3:14])[C@H:9]3[CH2:10][CH2:11][C:12]2=[O:22])[CH2:4]1)=[O:38])=[O:32])([CH3:29])([CH3:28])[CH3:27]

Participants

7

Reactant 4

HCID 14797Potassium HydroxideHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 2948944-(((Tert-butoxy)carbonyl)amino)butanoic acidHCID 69134041HCID 69134041, compound

Product 1

HCID 69133356HCID 69133356, compoundYield 75%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

A solution of 3β-aminoandrostane-6,17-dione hydrochloride (150 mg) in CH2Cl2 was treated with powdered KOH (25 mg) and stirred for 15 min. 4-(tert-Butoxycarbonylamino)butyric acid (98 mg), EDAC (168 mg) and 4-dimethylaminopyridine (8 mg) were added at 0° C. The reaction temperature was raised to room temperature and stirred for 24 hrs. The mixture was washed with water (2×10 mL) and 5% NaHCO3 (10 mL). The organic layer was dried and evaporated to dryness. The residue was purified by flash chromatography (SiO2; CH2Cl2:MeOH:NH3 9:1:0.1) to give 3β-[4-(tert-butoxycarbonylamino)butyramido]-androstane-6,17-dione (161 mg, 75%). 1H-NMR (300 MHz, DMSO-d6, ppm from TMS): δ 7.68 (1H, d), 6.77 (1H, t), 3.46 (1H, m), 2.87 (2H, m), 2.45-1.10 (24H, m), 1.36 (9H, s), 0.78 (3H, s), 0.66 (3H, s).

Workup

  1. stirringstirred for 24 hrs
  2. washThe mixture was washed with water (2×10 mL) and 5% NaHCO3 (10 mL)
  3. customThe organic layer was dried
  4. customevaporated to dryness
  5. customThe residue was purified by flash chromatography (SiO2; CH2Cl2:MeOH:NH3 9:1:0.1)

Sources & evidence

ORD record
ord-091afb1f5fef4a81b0022229b89b84b5
Source dataset
uspto-grants-2013_12
Patent number
US08609644B2

Reaction notes

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