Dimethylformamide → (R)-tert-butoxycarbonyl amino-(4-dimethylcarbamoyl methoxy-phenyl)-acetic acid

HRID 561970노트

반응식

HRID 561970 반응식
C(OC([NH:8][C@H:9]([C:13]1[CH:18]=[CH:17][C:16](OCCOC(C)(C)C)=[CH:15][CH:14]=1)[C:10]([OH:12])=[O:11])=O)(C)(C)C.ClC[C:29]([N:31]([CH3:33])[CH3:32])=[O:30].[H-].[Na+].[C:36]([O:40][C:41](N[C@@H](C1C=CC(O)=CC=1)C(O)=O)=[O:42])([CH3:39])([CH3:38])[CH3:37].CN(C)[CH:57]=[O:58]>O>[C:36]([O:40][C:41]([C@@:9]([NH2:8])([C:13]1[CH:14]=[CH:15][C:16]([C:29](=[O:30])[N:31]([CH3:33])[CH3:32])=[CH:17][C:18]=1[O:58][CH3:57])[C:10]([OH:12])=[O:11])=[O:42])([CH3:39])([CH3:38])[CH3:37]

참가 물질

7

반응물 5

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 758862-chloro-N,N-dimethylacetamide2회HCID 11300124(S)-2-((tert-butoxycarbonyl)amino)-2-(4-hydroxyphenyl)acetic acidHCID 66815165(R)-tert-butoxycarbonylamino-[4-(2-tert-butoxy-ethoxy)-phenyl]-acetic acid

생성물 1

HCID 67001678(R)-tert-butoxycarbonyl amino-(4-dimethylcarbamoyl methoxy-phenyl)-acetic acid수율 76%

시약·촉매·용매 1

HCID 962Water용매

실험 절차

Prepared by the same method as described in example 1, step 1-G for the preparation of (R)-tert-butoxycarbonylamino-[4-(2-tert-butoxy-ethoxy)-phenyl]-acetic acid except that 2-chloro-N,N-dimethyl-acetamide was used in place of 2-(2-iodo-ethoxy)-2-methyl-propane and the preparation performed as follows: Sodium hydride (0.88 g, 22 mmol, 60% in mineral oil) was added portionwise to a stirred and cooled (ice bath) solution of (S)-tert-butoxycarbonylamino-(4-hydroxy-phenyl)-acetic acid (2.67 g, 10 mmol) in N,N-dimethylformamide (50 mL). 2-Chloro-N,N-dimethyl-acetamide (1.22 g, 10 mmol) was added and the mixture was stirred for three days. The mixture was diluted with water and extracted with ether. The aqueous layer was acidified to pH=2 and extracted with ethyl acetate. The combined organic extracts were washed with water, brine, dried over sodium sulfate, filtered and following evaporation of the solvents (S)-tert-butoxycarbonylamino-(4-dimethylcarbamoylmethoxy-phenyl)-acetic acid was obtained as a white solid (2.68 g, 76%). HR-MS: calcd for C31H29BrClN5O4 [M+H+] 650.1164. Found 650.1166.

후처리

  1. customPrepared by the same method
  2. stirringthe mixture was stirred for three days
  3. extractionextracted with ether
  4. extractionextracted with ethyl acetate
  5. washThe combined organic extracts were washed with water, brine
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. customevaporation of the solvents (S)-tert-butoxycarbonylamino-(4-dimethylcarbamoylmethoxy-phenyl)-acetic acid

출처 및 근거

ORD 기록
ord-7e96352d35064f8999be22a6830bba21
출처 데이터셋
uspto-grants-2011_11
특허 번호
US08063085B2

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