Ammonia → HCID 58204709, compound

HRID 2044725Notes

Reaction equation

HRID 2044725 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-0ea6eed6745641e1869e8e14f27dfe7c
Source dataset
uspto-grants-2013_11
Patent number
US08586574B2

Reaction notes

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