Water → HCID 89726203, compound

HRID 926368Notes

Reaction equation

HRID 926368 reaction equation
[C:1]1([C@H:7]([NH:10][C:11]([C:13]2[CH:14]=[C:15]([C:22](=[O:27])C(Cl)(Cl)Cl)[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.[OH2:28].[OH-].[Na+]>O1CCCC1>[C:1]1([C@H:7]([NH:10][C:11]([C:13]2[CH:14]=[C:15]([C:22]([OH:27])=[O:28])[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

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 897339816-(2,2,2-trichloro-acetyl)-3,4-dihydro-1H-pyrrolo[2,1-c][1,4]oxazine-8-carboxylic acid ((R)-1-phenyl-propyl)-amide

Product 1

HCID 89726203HCID 89726203, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution 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 (Comp. No. 10a) (9.8 g, 22.8 mmol) in tetrahydrofuran (160 ml) was added water (160 ml) and sodium hydroxide (4.5 g, 114 mmol) and the mixture was stirred at reflux until complete conversion according to LC/MS (ca. 60 min). Approximately half of the solvents were evaporated in vacuo and the mixture was acidified with excess hydrochloric acid. The forming precipitate was filtered off, washed once with water and dried in vacuo to give 6.29 g (84%) of 8-((R)-1-phenyl-propylcarbamoyl)-3,4-dihydro-1H-pyrrolo[2,1-c][1,4]oxazine-6-carboxylic acid as white solid. LC/MS (method 4): Rt=1.14 min; m/z=329.26 (M+H+).

Workup

  1. temperatureat reflux until complete conversion
  2. customaccording to LC/MS (ca. 60 min)
  3. customApproximately half of the solvents were evaporated in vacuo
  4. filtrationThe forming precipitate was filtered off
  5. washwashed once with water
  6. customdried in vacuo

Sources & evidence

ORD record
ord-2d72d6c56c02401880284876fcf6f77e
Source dataset
uspto-grants-2016_03
Patent number
US09284333B2

Reaction notes

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