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Acetyl chloride → (3S)-3-amino-1-[4-[(3S)-3-amino-5-[(6-bromo-2-methoxy-1-naphthyl)methyl]-4-oxo-2,3-dihydro-1,5-benzodiazepine-1-carbonyl]benzoyl]-5-[(6-bromo-2-methoxy-1-naphthyl)methyl]-2,3-dihydro-1,5-benzodiazepin-4-one dihydrochloride

HRID 1481939
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인쇄 미리보기

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HRID 1481939 반응식
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8]([CH2:12][N:13]1[C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=3[N:17]([C:24](=[O:67])[C:25]3[CH:30]=[CH:29][C:28]([C:31]([N:33]4[C:39]5[CH:40]=[CH:41][CH:42]=[CH:43][C:38]=5[N:37]([CH2:44][C:45]5[C:54]6[C:49](=[CH:50][C:51]([Br:55])=[CH:52][CH:53]=6)[CH:48]=[CH:47][C:46]=5[O:56][CH3:57])[C:36](=[O:58])[C@@H:35]([NH:59]C(OC(C)(C)C)=O)[CH2:34]4)=[O:32])=[CH:27][CH:26]=3)[CH2:16][C@H:15]([NH:68]C(=O)OC(C)(C)C)[C:14]1=[O:76])=[C:7]([O:77][CH3:78])[CH:6]=[CH:5]2.C([Cl:82])(=O)C>CO>[ClH:82].[ClH:82].[NH2:59][C@H:35]1[CH2:34][N:33]([C:31](=[O:32])[C:28]2[CH:27]=[CH:26][C:25]([C:24]([N:17]3[C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=4[N:13]([CH2:12][C:8]4[C:9]5[C:4](=[CH:3][C:2]([Br:1])=[CH:11][CH:10]=5)[CH:5]=[CH:6][C:7]=4[O:77][CH3:78])[C:14](=[O:76])[C@@H:15]([NH2:68])[CH2:16]3)=[O:67])=[CH:30][CH:29]=2)[C:39]2[CH:40]=[CH:41][CH:42]=[CH:43][C:38]=2[N:37]([CH2:44][C:45]2[C:54]3[C:49](=[CH:50][C:51]([Br:55])=[CH:52][CH:53]=3)[CH:48]=[CH:47][C:46]=2[O:56][CH3:57])[C:36]1=[O:58]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

4

반응물 2

HCID 6367Acetyl chlorideHCID 90220903tert-butyl N-[(3S)-5-[(6-bromo-2-methoxy-1-naphthyl)methyl]-1-[4-[(3S)-5-[(6-bromo-2-methoxy-1-naphthyl)methyl]-3-(tert-butoxycarbonylamino)-4-oxo-2,3-dihydro-1,5-benzodiazepine-1-carbonyl]benzoyl]-4-oxo-2,3-dihydro-1,5-benzodiazepin-3-yl]carbamate

생성물 1

HCID 90220955(3S)-3-amino-1-[4-[(3S)-3-amino-5-[(6-bromo-2-methoxy-1-naphthyl)methyl]-4-oxo-2,3-dihydro-1,5-benzodiazepine-1-carbonyl]benzoyl]-5-[(6-bromo-2-methoxy-1-naphthyl)methyl]-2,3-dihydro-1,5-benzodiazepin-4-one dihydrochloride
수율 98.4%

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

tert-Butyl N-[(3S)-5-[(6-bromo-2-methoxy-1-naphthyl)methyl]-1-[4-[(3S)-5-[(6-bromo-2-methoxy-1-naphthyl)methyl]-3-(tert-butoxycarbonylamino)-4-oxo-2,3-dihydro-1,5-benzodiazepine-1-carbonyl]benzoyl]-4-oxo-2,3-dihydro-1,5-benzodiazepin-3-yl]carbamate (31 mg, 0.026 mmol) and acetyl chloride (9.3 μL, 0.131 mmol) were combined in MeOH (2 mL) and stirred at room temperature for 16 h. The mixture was concentrated to give (3S)-3-amino-1-[4-[(3S)-3-amino-5-[(6-bromo-2-methoxy-1-naphthyl)methyl]-4-oxo-2,3-dihydro-1,5-benzodiazepine-1-carbonyl]benzoyl]-5-[(6-bromo-2-methoxy-1-naphthyl)methyl]-2,3-dihydro-1,5-benzodiazepin-4-one dihydrochloride as a white solid (27 mg, 98%) that was used without further purification.

후처리

  1. concentrationThe mixture was concentrated

출처 및 근거

ORD 기록
ord-acef2d0fd33b4413a91640839842f6c2
출처 데이터셋
uspto-grants-2016_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09409888B2

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