Acetyl chloride → HCID 118677393, compound

HRID 1481927Notes

Reaction equation

HRID 1481927 reaction equation
[CH2:1]([NH:8][C:9]([C@@H:11]1[CH2:15][C@H:14]([NH:16][C:17](=[O:66])[C:18]2[CH:23]=[CH:22][C:21]([C:24]([N:26]3[C:32]4[CH:33]=[CH:34][CH:35]=[CH:36][C:31]=4[N:30]([CH2:37][C:38]4[C:47]5[C:42](=[CH:43][C:44]([Br:48])=[CH:45][CH:46]=5)[CH:41]=[CH:40][C:39]=4[O:49][CH3:50])[C:29](=[O:51])[C@@H:28]([NH:52][C:53](=[O:65])[C@@H:54]([N:56](C(OC(C)(C)C)=O)[CH3:57])[CH3:55])[CH2:27]3)=[O:25])=[CH:20][CH:19]=2)[CH2:13][N:12]1[C:67](=[O:89])[C@@H:68]([NH:75][C:76](=[O:88])[C@@H:77]([N:79](C)[C:80](=O)OC(C)(C)C)[CH3:78])[CH:69]1[CH2:74][CH2:73][CH2:72][CH2:71][CH2:70]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([Cl:93])(=O)C>CO>[ClH:93].[ClH:93].[CH2:1]([NH:8][C:9]([C@@H:11]1[CH2:15][C@H:14]([NH:16][C:17](=[O:66])[C:18]2[CH:23]=[CH:22][C:21]([C:24]([N:26]3[C:32]4[CH:33]=[CH:34][CH:35]=[CH:36][C:31]=4[N:30]([CH2:37][C:38]4[C:47]5[C:42](=[CH:43][C:44]([Br:48])=[CH:45][CH:46]=5)[CH:41]=[CH:40][C:39]=4[O:49][CH3:50])[C:29](=[O:51])[C@@H:28]([NH:52][C:53](=[O:65])[C@@H:54]([NH:56][CH3:57])[CH3:55])[CH2:27]3)=[O:25])=[CH:20][CH:19]=2)[CH2:13][N:12]1[C:67](=[O:89])[C@H:68]([CH:69]1[CH2:70][CH2:71][CH2:72][CH2:73][CH2:74]1)[NH:75][C:76](=[O:88])[C@@H:77]([NH:79][CH3:80])[CH3:78])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 6367Acetyl chlorideHCID 118677428HCID 118677428, compound

Product 1

HCID 118677393HCID 118677393, compoundYield 197.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To tert-butyl N-[(1S)-2-[[(1S)-2-[(2S,4S)-2-(benzylcarbamoyl)-4-[[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]amino]pyrrolidin-1-yl]-1-cyclohexyl-2-oxo-ethyl]amino]-1-methyl-2-oxo-ethyl]-N-methyl-carbamate (45 mg, 0.035 mmol) in methanol (2 mL) at room temperature was added acetyl chloride (25 μL, 0.035 mmol) dropwise. The mixture was allowed to stand at room temperature. After 16 h the mixture was concentrated and the residue was triturated with acetonitrile to give the title compound (40 mg, 98%) as a tan solid. MS: m/z 1085 (MH+)

Workup

  1. customto stand at room temperature
  2. concentrationAfter 16 h the mixture was concentrated
  3. customthe residue was triturated with acetonitrile

Sources & evidence

ORD record
ord-645d80c8cc554e4c8e86077b9be90127
Source dataset
uspto-grants-2016_08
Patent number
US09409888B2

Reaction notes

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