Water → HCID 89726819, compound

HRID 926358Notes

Reaction equation

HRID 926358 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[CH:7]=[C:8]([C:15](=[O:20])C(Cl)(Cl)Cl)[N:9]2[CH2:14][CH2:13][O:12][CH2:11][C:10]=12)=[O:5])[CH3:2].[OH2:21].[OH-].[K+]>O1CCCC1>[CH2:1]([O:3][C:4]([C:6]1[CH:7]=[C:8]([C:15]([OH:20])=[O:21])[N:9]2[CH2:14][CH2:13][O:12][CH2:11][C:10]=12)=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 962WaterHCID 14797Potassium Hydroxide2×HCID 897269186-(2,2,2-trichloro-acetyl)-3,4-dihydro-1H-pyrrolo[2,1-c][1,4]oxazine-8-carboxylic acid ethyl ester

Product 1

HCID 89726819HCID 89726819, compoundYield 85%

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 ethyl ester (Comp. No. 4a) (11 g, 32.3 mmol) in tetrahydrofuran (60 ml) was added water (110 ml) and potassium hydroxide (1.72 g, 30.7 mmol). The mixture was stirred for 5 min, then an additional portion of potassium hydroxide (250 mg) was added and the mixture was stirred for 2 h at 25° C. Tetrahydrofuran was evaporated in vacuo. After addition of 50 ml water, the mixture was acidified with 10 M aqueous hydrochloric acid. The precipitate was filtered off, washed with a small portion of water and dried in vacuo at 55° C. to give 6.56 g (85%) of 3,4-dihydro-1H-pyrrolo[2,1-c][1,4]oxazine-6,8-dicarboxylic acid 8-ethyl ester as a white solid. LC/MS (method 3): Rt=1.34 min; m/z=240.03 (M+H+).

Workup

  1. stirringthe mixture was stirred for 2 h at 25° C
  2. customTetrahydrofuran was evaporated in vacuo
  3. additionAfter addition of 50 ml water
  4. filtrationThe precipitate was filtered off
  5. washwashed with a small portion of water
  6. customdried in vacuo at 55° C.

Sources & evidence

ORD record
ord-972d0e067cef491fa2c80b53ed989f7c
Source dataset
uspto-grants-2016_03
Patent number
US09284333B2

Reaction notes

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