Acetic Anhydride → HCID 70913733, compound

HRID 1844754Notes

Reaction equation

HRID 1844754 reaction equation
[NH2:1][CH2:2][C:3]([C:6]1[CH:7]=[C:8]([C:16]2[N:20]([CH2:21][CH:22]3[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]3)[C:19]([CH3:28])=[C:18]([S:29]([NH2:32])(=[O:31])=[O:30])[CH:17]=2)[CH:9]=[C:10]([C:12]([CH3:15])([CH3:14])[CH3:13])[CH:11]=1)([CH3:5])[CH3:4].[CH3:33][C:34](OC(C)=O)=[O:35]>C(Cl)Cl>[C:12]([C:10]1[CH:11]=[C:6]([C:3]([CH3:4])([CH3:5])[CH2:2][NH:1][C:34](=[O:35])[CH3:33])[CH:7]=[C:8]([C:16]2[N:20]([CH2:21][CH:22]3[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]3)[C:19]([CH3:28])=[C:18]([S:29](=[O:31])(=[O:30])[NH2:32])[CH:17]=2)[CH:9]=1)([CH3:13])([CH3:14])[CH3:15]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 70913730HCID 70913730, compound

Product 1

HCID 70913733HCID 70913733, compoundYield 54.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of compound 48 (100 mg, 0.22 mmol) in dry DCM (5 mL) was added Ac2O (25 mg, 0.24 mmol) at 0° C. and then the solution was stirred overnight at rt, concentrated and purified by prep-TLC to afford compound 49 (60 mg, 54%) as a white solid. 1H-NMR (DMSO-d6, 400 MHz) δ: 0.64-0.67 (2H, m), 0.93-0.95 (3H, m), 1.26-1.30 (20H, m), 1.46 (3H, d, J=6.8 Hz), 1.77 (3H, s), 2.43 (3H, s), 3.28 (2H, d, J=5.6 Hz), 3.76 (3H, d, J=7.2 Hz), 6.28 (1H, s), 6.91 (2H, s), 7.09 (1H, s), 7.16 (1H, s), 7.35 (1H, s), 7.67 (1H, m). MS Calcd.: 501; MS Found: 502 (M+1).

Workup

  1. concentrationconcentrated
  2. custompurified by prep-TLC

Sources & evidence

ORD record
ord-b21e35b8a7084a50b4c5e32fd68f51fc
Source dataset
uspto-grants-2015_02
Patent number
US08946446B2

Reaction notes

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