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Acetic Acid → t-Butyl 4'-[[3(R)-[[3-amino-3-methyl-l-oxobutyl]amino]-2,3,4,5-tetrahydro-2-oxo-1H-1-benzazepin-1-yl]methyl][1,1'-biphenyl]-2-carboxylate acetate

HRID 1755791
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HRID 1755791 반응식
C(OC([NH:11][C:12]([CH3:50])([CH3:49])[CH2:13][C:14]([NH:16][C@@H:17]1[CH2:23][CH2:22][C:21]2[CH:24]=[CH:25][CH:26]=[CH:27][C:20]=2[N:19]([CH2:28][C:29]2[CH:34]=[CH:33][C:32]([C:35]3[C:36]([C:41]([O:43][C:44]([CH3:47])([CH3:46])[CH3:45])=[O:42])=[CH:37][CH:38]=[CH:39][CH:40]=3)=[CH:31][CH:30]=2)[C:18]1=[O:48])=[O:15])=O)C1C=CC=CC=1.C(O)(=O)C>CO.[OH-].[Pd+2].[OH-]>[C:41]([OH:43])(=[O:42])[CH3:36].[NH2:11][C:12]([CH3:50])([CH3:49])[CH2:13][C:14]([NH:16][C@@H:17]1[CH2:23][CH2:22][C:21]2[CH:24]=[CH:25][CH:26]=[CH:27][C:20]=2[N:19]([CH2:28][C:29]2[CH:30]=[CH:31][C:32]([C:35]3[C:36]([C:41]([O:43][C:44]([CH3:46])([CH3:45])[CH3:47])=[O:42])=[CH:37][CH:38]=[CH:39][CH:40]=3)=[CH:33][CH:34]=2)[C:18]1=[O:48])=[O:15]
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참가 물질

5

반응물 2

HCID 176Acetic AcidHCID 228551634'-[[2,3,4,5-Tetrahydro-3(R)-[[3-methyl-1-oxo-3-[[(benzyloxy)carbonyl]amino] butyl]amino]-2-oxo-1H-1-benzazepin-1-yl]methyl]-[1,1'-biphenyl]-2-carboxylic acid 1,1-dimethylethyl ester

생성물 1

HCID 67788487t-Butyl 4'-[[3(R)-[[3-amino-3-methyl-l-oxobutyl]amino]-2,3,4,5-tetrahydro-2-oxo-1H-1-benzazepin-1-yl]methyl][1,1'-biphenyl]-2-carboxylate acetate수율 193.7%

시약·촉매·용매 2

HCID 9942167
Palladium hydroxide
촉매
HCID 887Methanol용매

실험 절차

To a solution of 400 mg (0.592 mmol) of t-butyl 4'-[[3(R)[[3-benzyloxycarbonylamino-3-methyl-1-oxobutyl]amino]-2,3,4,5-tetrahydro-2-oxo-1H-1-benzazepin-1-yl]methyl][1,1'-biphenyl]-2-carboxylate (prepared according to the procedure of Fisher et al, U.S. Pat. No. 5,206,235) in 10 mL of methanol was added 0.034 mL (0.59 mmol) of acetic acid and 80 mg (20% w/w) palladium hydroxide. The resulting mixture was stirred under a hydrogen atmosphere for 4 hours. Catalyst was removed by filtration through Celite and the solvent removed under vacuum to afford 345 mg (97%) of the product as a white solid. 1H NMR (400 MHz, CD3OD): δ1.17 (s, 9H), 1.37 (s, 3H), 1.41 (s, 3H), 1.92 (s, 3H), 2.17 (m, 1H), 2.35 (m, 1H), 2.45-2.75 (m, 4H), 4.41 (dd; 12, 8 Hz; 1H), 4.93 (d, 15 Hz, 1H), 5.37 (d, 16 Hz, 1H), 7.12-7.52 (m, 11H), 7.66 (d, 8 Hz, 1H). FAB-MS: calculated for C33H39N3O4 541; found 542 (M+H,100%).

후처리

  1. customCatalyst was removed by filtration through Celite
  2. customthe solvent removed under vacuum

출처 및 근거

ORD 기록
ord-b3170d1a9ee44ca6ae5001a0d5e1a95a
출처 데이터셋
uspto-grants-1995_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05438136

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