Water → 3,4-dihydro-1H-pyrrolo[2,1-c][1,4]oxazine-6,8-dicarboxylic acid 8-ethyl ester

HRID 926358노트

반응식

HRID 926358 반응식
[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]

참가 물질

5

반응물 3

HCID 962WaterHCID 14797Potassium Hydroxide2회HCID 897269186-(2,2,2-trichloro-acetyl)-3,4-dihydro-1H-pyrrolo[2,1-c][1,4]oxazine-8-carboxylic acid ethyl ester

생성물 1

HCID 897268193,4-dihydro-1H-pyrrolo[2,1-c][1,4]oxazine-6,8-dicarboxylic acid 8-ethyl ester수율 85%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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+).

후처리

  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.

출처 및 근거

ORD 기록
ord-972d0e067cef491fa2c80b53ed989f7c
출처 데이터셋
uspto-grants-2016_03
특허 번호
US09284333B2

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