Ammonia → HCID 58204709, compound

HRID 1498565Notes

Reaction equation

HRID 1498565 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-5e7a34d2fbf14aff8d718d257a43fff5
Source dataset
uspto-grants-2015_12
Patent number
US09198918B2

Reaction notes

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