Acetyl chloride → HCID 90817132, compound

HRID 1169294Notes

Reaction equation

HRID 1169294 reaction equation
[C:1]1([C:11]2[CH:16]=[CH:15][C:14]([CH:17]([CH:35]3[CH2:40][CH2:39][NH:38][CH2:37][CH2:36]3)[CH2:18][N:19]([C:28](=[O:34])[C:29]([O:31][CH2:32][CH3:33])=[O:30])[CH2:20][CH2:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)=[CH:13][CH:12]=2)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.C(N(CC)CC)C.[C:48](Cl)(=[O:50])[CH3:49]>ClCCl>[C:48]([N:38]1[CH2:39][CH2:40][CH:35]([CH:17]([C:14]2[CH:13]=[CH:12][C:11]([C:1]3[C:10]4[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=4)[CH:4]=[CH:3][CH:2]=3)=[CH:16][CH:15]=2)[CH2:18][N:19]([C:28](=[O:34])[C:29]([O:31][CH2:32][CH3:33])=[O:30])[CH2:20][CH2:21][C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH2:36][CH2:37]1)(=[O:50])[CH3:49]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 91010650HCID 91010650, compound

Product 1

HCID 90817132HCID 90817132, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A room temperature solution of Example 47A (50.0 mg, 0.094 mmol) in dichloromethane (2 mL) was treated with triethylamine (26.2 μL, 0.19 mmol) and acetyl chloride (10.0 μL, 0.14 mmol), stirred for 1 hour, and concentrated. The concentrate was purified by flash column chromatography on silica gel with 4:1 hexanes/ethyl acetate to provide the desired product.

Workup

  1. concentrationconcentrated
  2. customThe concentrate was purified by flash column chromatography on silica gel with 4:1 hexanes/ethyl acetate

Sources & evidence

ORD record
ord-a43dcfd344d74472ba195222273f3ec4
Source dataset
uspto-grants-2003_09
Patent number
US06627767B2

Reaction notes

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