Trichloroacetyl chloride → HCID 89733981, compound

HRID 926367

Reaction equation

HRID 926367 reaction equation
[C:1]1([C@H:7]([NH:10][C:11]([C:13]2[CH:14]=[CH:15][N:16]3[CH2:21][CH2:20][O:19][CH2:18][C:17]=23)=[O:12])[CH2:8][CH3:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Cl:22][C:23]([Cl:28])([Cl:27])[C:24](Cl)=[O:25]>ClCCl>[C:1]1([C@H:7]([NH:10][C:11]([C:13]2[CH:14]=[C:15]([C:24](=[O:25])[C:23]([Cl:28])([Cl:27])[Cl:22])[N:16]3[CH2:21][CH2:20][O:19][CH2:18][C:17]=23)=[O:12])[CH2:8][CH3:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 6420Trichloroacetyl chloride2×HCID 1189460373,4-dihydro-1H-pyrrolo[2,1-c][1,4]oxazine-8-carboxylic acid ((R)-1-phenyl-propyl)-amide

Product 1

HCID 89733981HCID 89733981, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3,4-dihydro-1H-pyrrolo[2,1-c][1,4]oxazine-8-carboxylic acid ((R)-1-phenyl-propyl)-amide (Comp. No. 9a) (8.5 g, 29.9 mmol) in anhydrous dichloromethane (33 ml) was added trichloro-acetyl chloride (16.3 g, 89.7 mmol). The resulting mixture was stirred overnight at room temperature, after which a second portion of trichloro-acetyl chloride (3 ml) was added. The resulting mixture was stirred for 6 h at 40° C., and then at 25° C. over 2 days, evaporated to dryness. Methyl tert-butyl ether (60 ml) was added and the mixture was stirred. The product precipitated, was filtered off, washed with a small amount of methyl tert-butyl ether and dried in vacuo to give 9.8 g (76%) of 6-(2,2,2-trichloro-acetyl)-3,4-dihydro-1H-pyrrolo[2,1-c][1,4]oxazine-8-carboxylic acid ((R)-1-phenyl-propyl)-amide. LC/MS (method 4): Rt=1.34 min; m/z=429.01 (M+H+).

Workup

  1. stirringThe resulting mixture was stirred for 6 h at 40° C.
  2. waitat 25° C. over 2 days
  3. customevaporated to dryness
  4. additionMethyl tert-butyl ether (60 ml) was added
  5. stirringthe mixture was stirred
  6. customThe product precipitated
  7. filtrationwas filtered off
  8. washwashed with a small amount of methyl tert-butyl ether
  9. customdried in vacuo

Sources & evidence

ORD record
ord-5311df023b0b43b7b6f3116ed84edd45
Source dataset
uspto-grants-2016_03
Patent number
US09284333B2

Linked notes

Loading…