Acetic Anhydride → HCID 18512158, compound

HRID 1370851Notes

Reaction equation

HRID 1370851 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:7]=[C:8]([CH:37]=[CH:38][CH:39]=1)[O:9][C:10]1[CH:36]=[CH:35][C:13]([CH2:14][N:15]([CH2:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[C:16]2[C:17]([CH3:27])=[C:18]([NH:22][S:23]([CH3:26])(=[O:25])=[O:24])[CH:19]=[CH:20][CH:21]=2)=[CH:12][CH:11]=1.[C:40](OC(=O)C)(=[O:42])[CH3:41]>C(Cl)Cl>[CH2:28]([N:15]([CH2:14][C:13]1[CH:35]=[CH:36][C:10]([O:9][C:8]2[CH:7]=[C:6]([CH:39]=[CH:38][CH:37]=2)[O:5][CH2:4][CH2:3][CH2:2][NH:1][C:40](=[O:42])[CH3:41])=[CH:11][CH:12]=1)[C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([NH:22][S:23]([CH3:26])(=[O:25])=[O:24])[C:17]=1[CH3:27])[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 18512083HCID 18512083, compound

Product 1

HCID 18512158HCID 18512158, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The product from Example 70C (0.028 g, 0.0514 mmoles) in CH2Cl2 (1 mL) was treated with acetic anhydride (0.0060 mL, 0.0617 mmoles) and stirred overnight at room temperature. The reaction was concentrated under reduced pressure, and the residue was purified by preparative HPLC (CH3CN:0.1% trifluoroacetic acid in H2O) on a YMC ODS Guardpak column. 1H NMR (300 MHz, CDCl3) δ7.10-7.30 (m, 10 H), 6.96 (d, 1 H), 6.89 (d, 2 H), 6.60 (m, 2 H), 6.44 (t, 1 H), 6.29 (s, 1 H), 5.85 (br.s, 1 H), 4.09 (s, 2 H), 4.06 (s, 2 H), 3.98 (t, 2 H), 3.44 (dd, 2 H), 2.91 (s, 3 H), 2.31 (s, 3 H), 1.98 (s, 3 H), 1.90-2.10 (m, 2 H); MS (ESI+) mn/z 588 (M+H)+.

Workup

  1. concentrationThe reaction was concentrated under reduced pressure
  2. customthe residue was purified by preparative HPLC (CH3CN:0.1% trifluoroacetic acid in H2O) on a YMC ODS Guardpak column

Sources & evidence

ORD record
ord-4bc0710588f8462aa7767f6f877d35e6
Source dataset
uspto-grants-2003_06
Patent number
US06583180B2

Reaction notes

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