Ammonia → HCID 58204709, compound

HRID 886506Notes

Reaction equation

HRID 886506 reaction equation
C[O:2][C:3](=O)[C@@H:4]([O:14][C:15]1[CH:38]=[CH:37][C:18]2[C:19]3[N:23]([CH2:24][CH2:25][O:26][C:17]=2[CH:16]=1)[CH:22]=[C:21]([C:27]1[N:28]([CH2:32][C:33]([F:36])([F:35])[F:34])[N:29]=[CH:30][N:31]=1)[N:20]=3)[CH2:5][O:6][Si:7]([C:10]([CH3:13])([CH3:12])[CH3:11])([CH3:9])[CH3:8].[NH3:40]>CO>[C:10]([Si:7]([CH3:9])([CH3:8])[O:6][CH2:5][C@H:4]([O:14][C:15]1[CH:38]=[CH:37][C:18]2[C:19]3[N:23]([CH2:24][CH2:25][O:26][C:17]=2[CH:16]=1)[CH:22]=[C:21]([C:27]1[N:28]([CH2:32][C:33]([F:34])([F:36])[F:35])[N:29]=[CH:30][N:31]=1)[N:20]=3)[C:3]([NH2:40])=[O:2])([CH3:11])([CH3:12])[CH3:13]

Participants

4

Reactant 2

HCID 222AmmoniaHCID 67050848(S)-3-(tert-Butyl-dimethyl-silanyloxy)-2-{2-[2-(2,2,2-trifluoro-ethyl)-2H-[1,2,4]triazol-3-yl]-4,5-dihydro-6-oxa-1,3a-diaza-benzo[e]azulen-8-yloxy}-propionic acid methyl ester

Product 1

HCID 58204709HCID 58204709, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

(S)-3-(tert-Butyl-dimethyl-silanyloxy)-2-{2-[2-(2,2,2-trifluoro-ethyl)-2H-[1,2,4]triazol-3-yl]-4,5-dihydro-6-oxa-1,3a-diaza-benzo[e]azulen-8-yloxy}-propionic acid methyl ester was dissolved in ammonia in methanol (7 N, 10 mL) and the reaction mixture stirred at RT for 48 hr. The reaction mixture was concentrated in vacuo and the resultant residue subjected to flash chromatography (SiO2, gradient 0-5% methanol in ethyl acetate) to give (S)-3-(tert-Butyl-dimethyl-silanyloxy)-2-{2-[2-(2,2,2-trifluoro-ethyl)-2H-[1,2,4]triazol-3-yl]-4,5-dihydro-6-oxa-1,3a-diaza-benzo[e]azulen-8-yloxy}-propionamide as a yellow oil (101 mg, 49% over 2 steps). LCMS: RT=3.78 min, [M+H]+=553

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo

Sources & evidence

ORD record
ord-1b3a8f13cee84c3fa2e0dc97b5db8e86
Source dataset
uspto-grants-2012_08
Patent number
US08242104B2

Reaction notes

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