Acetyl chloride → HCID 9984384, compound

HRID 723449Notes

Reaction equation

HRID 723449 reaction equation
[CH3:1][N:2]([CH2:4][C:5]1[CH:39]=[CH:38][C:8]([O:9][CH2:10][C:11]([N:13]2[CH2:18][CH2:17][N:16]([C:19]3[CH:24]=[CH:23][C:22]([N:25]4[CH2:29][C@H:28]([CH2:30][NH:31][C:32](=S)[CH2:33]C)[O:27][C:26]4=[O:36])=[CH:21][C:20]=3[F:37])[CH2:15][CH2:14]2)=[O:12])=[CH:7][CH:6]=1)[CH3:3].C(Cl)(=[O:42])C>C(N(CC)CC)C>[CH3:1][N:2]([CH2:4][C:5]1[CH:6]=[CH:7][C:8]([O:9][CH2:10][C:11]([N:13]2[CH2:14][CH2:15][N:16]([C:19]3[CH:24]=[CH:23][C:22]([N:25]4[CH2:29][C@H:28]([CH2:30][NH:31][C:32](=[O:42])[CH3:33])[O:27][C:26]4=[O:36])=[CH:21][C:20]=3[F:37])[CH2:17][CH2:18]2)=[O:12])=[CH:38][CH:39]=1)[CH3:3]

Participants

4

Reactant 2

HCID 6367Acetyl chlorideHCID 58745346HCID 58745346, compound

Product 1

HCID 9984384HCID 9984384, compound

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

As described for the preparation of 27, the reaction of 26 (prepared from 264 mg of 25) with acetyl chloride and triethylamine gave the acetamide which was purified by silica gel chromatography with 5% MeOH-0.5%NH4OH—CH2Cl2 followed by crystallization from Et2OAc to give 73 mg of 29, a white solid; 1HNMR [300 MHz, (CD3)2SO] δ 1.81 (s, 3H), 2.45 (s, 6H), 2.93. 3.00 (s, s, 4H), 3.38 (t, 2H), 3.60 (s, 4H), 3.68 (dd, 1H), 3.85 (s, 2H), 4.06 (t, 1H), 4.69 (m, 1H), 4.88 (s, 2H), 6.94 (d, 2H), 7.06 (t, 1H), 7.16 (dd, 1H), 7.33 (d, 2H), 7.49 (dd, 1H), 8.24 (t, 1H).

Sources & evidence

ORD record
ord-fd733db4f5c74e30bc4ee197cdda1a11
Source dataset
uspto-grants-2006_11
Patent number
US07141570B2

Reaction notes

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