Ammonia methanol → [2-Carbamoyl-9-(3-hydroxy-3-methyl-but-1-ynyl)-4,5-dihydro-6-oxa-3-thia-1-aza-benzo[e]azulen-4-yl]-acetic acid methyl ester

HRID 575125Notes

Reaction equation

HRID 575125 reaction equation
C[O:2][C:3]([C:5]1[S:6][C:7]2[CH:8]([CH2:25][C:26]([O:28][CH3:29])=[O:27])[CH2:9][O:10][C:11]3[CH:18]=[CH:17][C:16]([C:19]#[C:20][C:21]([OH:24])([CH3:23])[CH3:22])=[CH:15][C:12]=3[C:13]=2[N:14]=1)=O.CO.[NH3:32]>>[CH3:29][O:28][C:26](=[O:27])[CH2:25][CH:8]1[C:7]2[S:6][C:5]([C:3](=[O:2])[NH2:32])=[N:14][C:13]=2[C:12]2[CH:15]=[C:16]([C:19]#[C:20][C:21]([OH:24])([CH3:22])[CH3:23])[CH:17]=[CH:18][C:11]=2[O:10][CH2:9]1

Participants

3

Reactant 2

HCID 21705897Ammonia methanolHCID 866931489-(3-Hydroxy-3-methyl-but-1-ynyl)-4-methoxycarbonylmethyl-4,5-dihydro-6-oxa-3-thia-1-aza-benzo[e]azulene-2-carboxylic acid methyl ester

Product 1

HCID 86693150[2-Carbamoyl-9-(3-hydroxy-3-methyl-but-1-ynyl)-4,5-dihydro-6-oxa-3-thia-1-aza-benzo[e]azulen-4-yl]-acetic acid methyl ester

Procedure

A solution of 9-(3-Hydroxy-3-methyl-but-1-ynyl)-4-methoxycarbonylmethyl-4,5-dihydro-6-oxa-3-thia-1-aza-benzo[e]azulene-2-carboxylic acid methyl ester (70 mg, 0.117 mmol) in methanol-ammonia (40 mL) was stirred at room temperature for 2 h. Then the mixture was concentrated to afford crude compound which was purified by flash column chromatography (silica gel, EtOAc in hexane from 10% to 20%) to afford [2-Carbamoyl-9-(3-hydroxy-3-methyl-but-1-ynyl)-4,5-dihydro-6-oxa-3-thia-1-aza-benzo[e]azulen-4-yl]-acetic acid methyl ester as light yellow oil. LC-MS (ESI & APCI): 401.4 (M+1).

Workup

  1. concentrationThen the mixture was concentrated
  2. customto afford crude compound which
  3. customwas purified by flash column chromatography (silica gel, EtOAc in hexane from 10% to 20%)

Sources & evidence

ORD record
ord-511c6523bfa54e32bc2100326fca3d07
Source dataset
uspto-grants-2015_05
Patent number
US09034866B2

Reaction notes

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