Acetyl chloride → HCID 118677384, compound

HRID 1481940Notes

Reaction equation

HRID 1481940 reaction equation
[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:73])[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:60](=[O:72])[C@@H:61]([N:63](C(OC(C)(C)C)=O)[CH3:64])[CH3:62])[CH2:34]4)=[O:32])=[CH:27][CH:26]=3)[CH2:16][C@H:15]([NH:74][C:75](=[O:87])[C@@H:76]([N:78](C)[C:79](=O)OC(C)(C)C)[CH3:77])[C:14]1=[O:88])=[C:7]([O:89][CH3:90])[CH:6]=[CH:5]2.C([Cl:94])(=O)C>CO>[ClH:94].[ClH:94].[Br:55][C:51]1[CH:50]=[C:49]2[C:54](=[CH:53][CH:52]=1)[C:45]([CH2:44][N:37]1[C:38]3[CH:43]=[CH:42][CH:41]=[CH:40][C:39]=3[N:33]([C:31](=[O:32])[C:28]3[CH:27]=[CH:26][C:25]([C:24]([N:17]4[C:18]5[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=5[N:13]([CH2:12][C:8]5[C:9]6[C:4](=[CH:3][C:2]([Br:1])=[CH:11][CH:10]=6)[CH:5]=[CH:6][C:7]=5[O:89][CH3:90])[C:14](=[O:88])[C@@H:15]([NH:74][C:75](=[O:87])[C@@H:76]([NH:78][CH3:79])[CH3:77])[CH2:16]4)=[O:73])=[CH:30][CH:29]=3)[CH2:34][C@H:35]([NH:59][C:60](=[O:72])[C@@H:61]([NH:63][CH3:64])[CH3:62])[C:36]1=[O:58])=[C:46]([O:56][CH3:57])[CH:47]=[CH:48]2

Participants

4

Reactant 2

HCID 6367Acetyl chlorideHCID 118677396HCID 118677396, compound

Product 1

HCID 118677384HCID 118677384, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

tert-Butyl N-[(1S)-2-[[(3S)-5-[(6-bromo-2-methoxy-1-naphthyl)methyl]-1-[4-[(3S)-5-[(6-bromo-2-methoxy-1-naphthyl)methyl]-3-[[(2S)-2-[tert-butoxycarbonyl(methyl)amino]propanoyl]amino]-4-oxo-2,3-dihydro-1,5-benzodiazepine-1-carbonyl]benzoyl]-4-oxo-2,3-dihydro-1,5-benzodiazepin-3-yl]amino]-1-methyl-2-oxo-ethyl]-N-methyl-carbamate (24 mg, 0.018 mmol) and acetyl chloride (6.3 μL, 0.089 mmol) were combined in MeOH (2 mL) and stirred at room temperature overnight. The mixture was concentrated and the residue triturated with acetonitrile to give the title compound (18.3 mg, 84%) as a solid. LC-MS: 1149 [M−H].

Workup

  1. concentrationThe mixture was concentrated
  2. customthe residue triturated with acetonitrile

Sources & evidence

ORD record
ord-edf88cbcebe0407882a9e868e0ab969e
Source dataset
uspto-grants-2016_08
Patent number
US09409888B2

Reaction notes

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