Triethylamine → 4-acetylamino-5-chloro-2-methoxy-N-[(2S,4S)-1-acetyl-2-hydroxymethyl-4-pyrrolidinyl]benzamide

HRID 1723904노트

반응식

HRID 1723904 반응식
[C:1]([NH:4][C:5]1[C:13]([Cl:14])=[CH:12][C:8]([C:9]([OH:11])=O)=[C:7]([O:15][CH3:16])[CH:6]=1)(=[O:3])[CH3:2].C(N(CC)CC)C.C(Cl)(=O)OCC.[C:30]([N:33]1[CH2:37][C@@H:36]([NH2:38])[CH2:35][C@H:34]1[CH2:39][OH:40])(=[O:32])[CH3:31]>ClCCl.O>[C:1]([NH:4][C:5]1[C:13]([Cl:14])=[CH:12][C:8]([C:9]([NH:38][C@@H:36]2[CH2:37][N:33]([C:30](=[O:32])[CH3:31])[C@H:34]([CH2:39][OH:40])[CH2:35]2)=[O:11])=[C:7]([O:15][CH3:16])[CH:6]=1)(=[O:3])[CH3:2]

참가 물질

7

반응물 4

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 109884964-Acetamido-5-chloro-2-methoxybenzoic acidHCID 450861111-((2S,4S)-4-Amino-2-(hydroxymethyl)pyrrolidin-1-yl)ethanone

생성물 1

HCID 117406984-acetylamino-5-chloro-2-methoxy-N-[(2S,4S)-1-acetyl-2-hydroxymethyl-4-pyrrolidinyl]benzamide수율 75.7%

시약·촉매·용매 2

HCID 962Water용매HCID 6344Dichloromethane용매2회

실험 절차

9.84 g of 4-acetylamino-5-chloro-2-methoxybenzoic acid, and 4.5 g of triethylamine were dissolved in 40 ml of dichloromethane, and 4.60 g of ethyl chlorocarbonate was added dropwise to the solution at not higher than 10° C. After stirring at the same temperature for 30 minutes, a solution of 7.03 g of (2S,4S)-(−)-1-acetyl-4-amino-2-hydroxymethylpyrrolidine in dichloromethane (20 ml) was added dropwise. After stirring at the same temperature overnight, water (20 ml) was added, precipitated crystals were filtered, and the resulting crystals were dried in a warm air at 50 to 55° C. to obtain 11.74 g of 4-acetylamino-5-chloro-2-methoxy-N-[(2S,4S)-1-acetyl-2-hydroxymethyl-4-pyrrolidinyl]benzamide.

후처리

  1. additionwas added
  2. customprecipitated crystals
  3. filtrationwere filtered
  4. customthe resulting crystals were dried in a warm air at 50 to 55° C.

출처 및 근거

ORD 기록
ord-a6d4b715b88c4437a32da0ff07774102
출처 데이터셋
uspto-grants-2009_02
특허 번호
US07485665B2

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