Di-tert-butyl dicarbonate → HCID 86690377, compound

HRID 513887Notes

Reaction equation

HRID 513887 reaction equation
[C:1]([O:4][C@H:5]1[CH2:22][CH2:21][C@@:20]2([CH3:23])[C@@H:7]([CH2:8][CH2:9][C@:10]3([CH3:35])[C@@H:19]2[CH2:18][CH2:17][C@H:16]2[C@@:11]3([CH3:34])[CH2:12][CH2:13][C@@:14]3([CH2:31][CH2:32][NH2:33])[CH2:26][C:25](=[O:27])[C:24]([CH:28]([CH3:30])[CH3:29])=[C:15]32)[C:6]1([CH3:37])[CH3:36])(=[O:3])[CH3:2].[O:38](C(OC(C)(C)C)=O)[C:39]([O:41][C:42]([CH3:45])([CH3:44])[CH3:43])=O>ClCCl>[C:1]([O:4][C@H:5]1[CH2:22][CH2:21][C@@:20]2([CH3:23])[C@@H:7]([CH2:8][CH2:9][C@:10]3([CH3:35])[C@@H:19]2[CH2:18][CH2:17][C@H:16]2[C@@:11]3([CH3:34])[CH2:12][CH2:13][C@@:14]3([CH2:31][CH2:32][NH:33][C:39]([O:41][C:42]([CH3:45])([CH3:44])[CH3:43])=[O:38])[CH2:26][C:25](=[O:27])[C:24]([CH:28]([CH3:30])[CH3:29])=[C:15]32)[C:6]1([CH3:36])[CH3:37])(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 90495Di-tert-butyl dicarbonateHCID 86690374HCID 86690374, compound

Product 1

HCID 86690377HCID 86690377, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
20 °C

Procedure

To a solution of (3aR,5aR,5bR,7aR,9S,11aR,11bR,13aS)-3a-(2-aminoethyl)-1-isopropyl-5a,5b,8,8,11a-pentamethyl-2-oxo-3,3a,4,5,5a,5b,6,7,7a,8,9,10,11,11a,11b,12,13,13a-octadecahydro-2H-cyclopenta[a]chrysen-9-yl acetate (34) (5.3 g, 10.36 mmol), TEA (2.165 mL, 15.53 mmol) and TEA (2.165 mL, 15.53 mmol) in dichloromethane (DCM) (100 mL) stirred at room temp was added BOC2O (2.404 mL, 10.36 mmol). The reaction mixture was stirred at 20° C. for 2 h. The reaction mixture was poured into ice water (300 ml) and the solids were collected and dried to give (3aR,5aR,5bR,7aR,9S,11aR,11bR,13aS)-3a-(2-((tert-butoxycarbonyl)amino)ethyl)-1-isopropyl-5a,5b,8,8,11a-pentamethyl-2-oxo-3,3a,4,5,5a,5b,6,7,7a,8,9,10,11,11a,11b,12,13,13a-octadecahydro-2H-cyclopenta[a]chrysen-9-yl acetate (35) (5.8 g, 8.34 mmol, 81% yield) as a white foam. This was ssed crude in next reaction without further purification. 1H NMR (400 MHz, CHLOROFORM-d) b=4.58-4.37 (m, 2H), 3.26-2.96 (m, 4H), 2.93-2.72 (m, 2H), 2.28 (d, J=18.8 Hz, 1H), 2.11-0.71 (m, 53H); LC/MS: m/z calculated 611.5. found 634.3 (M+Na)+.

Workup

  1. customthe solids were collected
  2. customdried

Sources & evidence

ORD record
ord-2c9f87ee3f7e47c18a71199ed419853e
Source dataset
uspto-grants-2015_08
Patent number
US09102685B2

Reaction notes

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