Lithium Hydroxide → 4-[[(2,6-dichlorophenyl)carbonyl]amino]-N-[[2-chloro-4-[5-[[(3-hydroxyphenyl)methyl]amino]-1H-tetrazol-1-yl]phenyl]carbonyl]-L-phenylalanine

HRID 1976957노트

반응식

HRID 1976957 반응식
[OH-].[Li+].C[O:4][C:5](=[O:49])[C@H:6]([CH2:31][C:32]1[CH:37]=[CH:36][C:35]([NH:38][C:39]([C:41]2[C:46]([Cl:47])=[CH:45][CH:44]=[CH:43][C:42]=2[Cl:48])=[O:40])=[CH:34][CH:33]=1)[NH:7][C:8]([C:10]1[CH:15]=[CH:14][C:13]([N:16]2[C:20]([NH:21][CH2:22][C:23]3[CH:28]=[CH:27][CH:26]=[C:25]([OH:29])[CH:24]=3)=[N:19][N:18]=[N:17]2)=[CH:12][C:11]=1[Cl:30])=[O:9]>CO.C1COCC1.O>[Cl:47][C:46]1[CH:45]=[CH:44][CH:43]=[C:42]([Cl:48])[C:41]=1[C:39]([NH:38][C:35]1[CH:34]=[CH:33][C:32]([CH2:31][C@@H:6]([C:5]([OH:49])=[O:4])[NH:7][C:8]([C:10]2[CH:15]=[CH:14][C:13]([N:16]3[C:20]([NH:21][CH2:22][C:23]4[CH:28]=[CH:27][CH:26]=[C:25]([OH:29])[CH:24]=4)=[N:19][N:18]=[N:17]3)=[CH:12][C:11]=2[Cl:30])=[O:9])=[CH:37][CH:36]=1)=[O:40]

참가 물질

6

반응물 2

HCID 3939Lithium HydroxideHCID 698493244-[[(2,6-dichlorophenyl)carbonyl]amino]-N-[[2-chloro-4-[5-[[(3-hydroxyphenyl)methyl]amino]-1H-tetrazol-1-yl]phenyl]carbonyl]-L-phenylalanine methyl ester

생성물 1

HCID 540037814-[[(2,6-dichlorophenyl)carbonyl]amino]-N-[[2-chloro-4-[5-[[(3-hydroxyphenyl)methyl]amino]-1H-tetrazol-1-yl]phenyl]carbonyl]-L-phenylalanine수율 77.5%

시약·촉매·용매 3

HCID 887Methanol용매HCID 962Water용매HCID 8028Tetrahydrofuran용매

실험 절차

An aqueous 1N lithium hydroxide solution (0.33 mL) was added to a solution of 4-[[(2,6-dichlorophenyl)carbonyl]amino]-N-[[2-chloro-4-[5-[[(3-hydroxyphenyl)methyl]amino]-1H-tetrazol-1-yl]phenyl]carbonyl]-L-phenylalanine methyl ester (75 mg; 0.108 mmol) in methanol (0.66 mL) and THF (0.66 mL) and the mixture was stirred at room temperature for 90 min. After the solvents were stripped under reduced pressure, the residue was dissolved in water (20 mL) and extracted with diethyl ether (3×5 mL). The aqueous layer was filtered through Celite, then acidified with 1 N HCl (0.35 mL). The resulting colorless solid was filtered off, washed with water, and dried in vacuo to give 57 mg of 4-[[(2,6-dichlorophenyl)carbonyl]amino]-N-[[2-chloro-4-[5-[[(3-hydroxyphenyl)methyl]amino]-1H-tetrazol-1-yl]phenyl]carbonyl]-L-phenylalanine. FAB HRMS: (C31H24Cl3N7O5) Obs. Mass 680.0981 Calcd. Mass 680.0983 (M+H).

후처리

  1. extractionextracted with diethyl ether (3×5 mL)
  2. filtrationThe aqueous layer was filtered through Celite
  3. filtrationThe resulting colorless solid was filtered off
  4. washwashed with water
  5. customdried in vacuo

출처 및 근거

ORD 기록
ord-a3fec1f3b0ca418890ecc0347040f6f3
출처 데이터셋
uspto-grants-2001_05
특허 번호
US06229011B1

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