Ethyl isocyanate → HCID 68725794, compound

HRID 2381028Notes

Reaction equation

HRID 2381028 reaction equation
[CH3:1][O:2][C:3](=[O:35])[C:4]([NH:7][C:8](=[O:34])[C@@H:9]([NH:26][C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[CH2:10][C:11]1[CH:16]=[CH:15][C:14]([O:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[C:13]([OH:25])[CH:12]=1)([CH3:6])[CH3:5].[CH2:36]([N:38]=[C:39]=[O:40])[CH3:37]>ClCCl.CN(C1C=CN=CC=1)C>[CH3:1][O:2][C:3](=[O:35])[C:4]([NH:7][C:8](=[O:34])[C@@H:9]([NH:26][C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[CH2:10][C:11]1[CH:16]=[CH:15][C:14]([O:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[C:13]([O:25][C:39](=[O:40])[NH:38][CH2:36][CH3:37])[CH:12]=1)([CH3:6])[CH3:5]

Participants

5

Reactant 2

HCID 8022Ethyl isocyanateHCID 68725930HCID 68725930, compound

Product 1

HCID 68725794HCID 68725794, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
50 °C

Procedure

2-[(S)-3-(4-benzyloxy-3-hydroxy-phenyl)-2-tert-butoxycarbonylamino-propionylamino]-2-methyl-propionic acid methyl ester (1.2 mmol), was dissolved in dichloromethane (5 ml) and ethyl isocyanate (0.31 ml) added. A catalytic amount of DMAP was added and the solution was heated at 50° C. for 7 hours. The reaction mixture was evaporated to dryness and the crude product purified by chromatography on silica gel eluting with a mixture of ethyl acetate-hexane. 2-[(S)-3-(4-Benzyloxy-3-ethylcarbamoyloxy-phenyl)-2-tert-butoxycarbonylaminopropionyl-amino]-2-methyl-propionic acid methyl ester was obtained as a white crystalline solid, 410 mg; Rf 0.29 (ethyl acetate-hexane 1:1); NMR (500 MHz, CDCl3) 1.39 (ca 3H, s), 1.41 (ca 3H, s), 1.43 (ca 9H, s), 2.86 (1H, dd J 14, 8), 3.08 (1H, dd J 14, 5), 3.25-3.32 (2H, m), 3.70 (3H, s), 4.23 (1H, br), 5.00 (1H, br t J 5), 5.07 (2H, s), 6.15 (1H, s), 6.91 (1H, d J 8), 6.99-7.02 (2H, m), 7.28-7.42 (ca 5H, m); HPLC/MS retention time 5.98 min, m/z 558 (MH+).

Workup

  1. customThe reaction mixture was evaporated to dryness
  2. customthe crude product purified by chromatography on silica gel eluting with a mixture of ethyl acetate-hexane

Sources & evidence

ORD record
ord-0dcbb08b3b72481d88cfc107966d02ec
Source dataset
uspto-grants-2012_09
Patent number
US08258097B2

Reaction notes

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