Diisopropylethylamine → (S)-2-{4'-[(5-cyano-4-methoxy-3-methyl-benzofuran-2-carbonyl)-amino]-biphenyl-4-sulfonylamino}-3-methyl-butyric acid methyl ester

HRID 29421노트

반응식

HRID 29421 반응식
[C:1]([C:3]1[CH:4]=[CH:5][C:6]2[O:10][C:9]([C:11]([OH:13])=O)=[C:8]([CH3:14])[C:7]=2[C:15]=1[O:16][CH3:17])#[N:2].[CH3:18][O:19][C:20](=[O:42])[C@@H:21]([NH:25][S:26]([C:29]1[CH:34]=[CH:33][C:32]([C:35]2[CH:40]=[CH:39][C:38]([NH2:41])=[CH:37][CH:36]=2)=[CH:31][CH:30]=1)(=[O:28])=[O:27])[CH:22]([CH3:24])[CH3:23].F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.C(N(CC)C(C)C)(C)C>[Cl-].[Na+].O.CN(C=O)C>[CH3:18][O:19][C:20](=[O:42])[C@@H:21]([NH:25][S:26]([C:29]1[CH:34]=[CH:33][C:32]([C:35]2[CH:36]=[CH:37][C:38]([NH:41][C:11]([C:9]3[O:10][C:6]4[CH:5]=[CH:4][C:3]([C:1]#[N:2])=[C:15]([O:16][CH3:17])[C:7]=4[C:8]=3[CH3:14])=[O:13])=[CH:39][CH:40]=2)=[CH:31][CH:30]=1)(=[O:28])=[O:27])[CH:22]([CH3:24])[CH3:23]

참가 물질

7

반응물 4

HCID 81531DiisopropylethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 59847687(S)-2-(4'-amino-biphenyl-4-sulfonylamino)-3-methyl-butyric acid methyl esterHCID 687164515-Cyano-4-methoxy-3-methyl-benzofuran-2-carboxylic acid

생성물 1

HCID 68711753(S)-2-{4'-[(5-cyano-4-methoxy-3-methyl-benzofuran-2-carbonyl)-amino]-biphenyl-4-sulfonylamino}-3-methyl-butyric acid methyl ester수율 32.2%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 57417360Sodium chloride; water용매

실험 절차

To 110 mg (0.48 mmol) of 5-cyano-4-methoxy-3-methyl-benzofuran-2-carboxylic acid was added 207 mg (1.2 eq) of (S)-2-(4′-amino-biphenyl-4-sulfonylamino)-3-methyl-butyric acid methyl ester, BOP (252 mg, 1.2 eq), N,N-diisopropylethylamine (74 mg,1.2 eq) and 4 mL of DMF. The mixture was stirred at room temperature for 48 h. Brine was added and the mixture was extracted with ethyl acetate. The combined organic solution was washed with 2N HCl and water. Concentration of the organics in vacuo gave crude product, which was purified by column chromatography on silica gel to give 89 mg (32% yield) of (S)-2-{4′-[(5-cyano-4-methoxy-3-methyl-benzofuran-2-carbonyl)-amino]-biphenyl-4-sulfonylamino}-3-methyl-butyric acid methyl ester as an off-white solid.

후처리

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe combined organic solution was washed with 2N HCl and water
  3. customConcentration of the organics in vacuo gave crude product, which
  4. customwas purified by column chromatography on silica gel

출처 및 근거

ORD 기록
ord-c54b20cf3d2e4e309f11fefb1ed5709b
출처 데이터셋
uspto-grants-2008_09
특허 번호
US07420001B2

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