Acetyl chloride → HCID 10462719, compound

HRID 2380146Notes

Reaction equation

HRID 2380146 reaction equation
[CH2:1]([O:8][N:9]([C:16](=[O:51])[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][N:24]([O:43][CH2:44][C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1)[C:25](=[O:42])[CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][NH:33][O:34][CH2:35][C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)[CH2:10][CH2:11][CH2:12][CH2:13][C:14]#[N:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:52](Cl)(=[O:54])[CH3:53].C(ON(CCCCC#N)C(=O)CCCCCl)C1C=CC=CC=1>CCOC(C)=O.CCCCCC>[CH2:1]([O:8][N:9]([C:16](=[O:51])[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][N:24]([O:43][CH2:44][C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1)[C:25](=[O:42])[CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][N:33]([O:34][CH2:35][C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)[C:52](=[O:54])[CH3:53])[CH2:10][CH2:11][CH2:12][CH2:13][C:14]#[N:15])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 10087530N-(Benzyloxy)-N-(4-cyanobutyl)-5-chloropentanamideHCID 10484855HCID 10484855, compound

Product 1

HCID 10462719HCID 10462719, compound

Reagents, catalysts & solvents 1

HCID 21226206Ethyl acetate hexaneSolvent

Procedure

Compound [VI] (0.93 g, 1.33 mmol) was treated with acetyl chloride (0.160 g, 2.04 mmol) by the procedure used for (3). Silica gel column chromatography (3:1 EtOAc/hexane) produced 0.95 g (96%) of [VII] as an oil: NMR δ 1.17-1.87 (m, 24H), 2.07 (s, 3H), 2.27-2.47 (m, 6H), 3.47-3.73 (m, 6H), 4.77 (s, 6H), 7.33 (s, 15H). Anal. (C44H60N4O6) C, H, N.

Sources & evidence

ORD record
ord-41ac3dbfedf84b28b71abf140feb5116
Source dataset
uspto-grants-1994_11
Patent number
US05364965

Reaction notes

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