Acetic Anhydride → HCID 56622940, compound

HRID 1422115Notes

Reaction equation

HRID 1422115 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[C:19]3=[C:20]([C:31]([OH:33])=[O:32])[C:21]([C:28]([OH:30])=O)=[C:22]4[CH:23]=[CH:24][C:25]([CH2:26][OH:27])=[C:17]([N:18]34)[CH:16]=2)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:34](OC(=O)C)(=[O:36])[CH3:35]>>[C:34]([O:27][CH2:26][C:25]1[CH:24]=[CH:23][C:22]2[N:18]3[C:19]([C:15]([C:12]4[CH:11]=[CH:10][C:9]([O:8][CH2:1][C:2]5[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=5)=[CH:14][CH:13]=4)=[CH:16][C:17]=13)=[C:20]1[C:31](=[O:32])[O:33][C:28](=[O:30])[C:21]1=2)(=[O:36])[CH3:35]

Participants

3

Reactant 2

HCID 7918Acetic AnhydrideHCID 18707032HCID 18707032, compound

Product 1

HCID 56622940HCID 56622940, compound

Procedure

The general synthetic pathway outlined in example 81, step 5, and example 83 have been applied to proper starting materials in the preparation of 3-(4-benzyloxyphenyl)-5-hydroxymethylpyrrolo[2,1,5-cd]indolizine-1,2-dicarboxylic acid, which was reacted with acetic acid anhydride by the general synthetic principles outlined in example 23, step 8, to afford 5-acetoxymethyl-3-(4-benzyloxyphenyl)pyrrolo[2,1,5-cd]indolizine-1,2-dicarboxylic acid anhydride as red crystals in 86%. 1H-NMR (DMSO-d6, 300 MHz) δ: 2.17 (s, 3H); 5.22 (s, 2H); 5.67 (s, 2H); 7.19 (d, 2H); 7.32-7.48 (m, 3H); 7.52 (d, 2H); 8.10-8.19 (m, 2H); 8.27 (d, 2H); 8.34 (d, 1H).

Sources & evidence

ORD record
ord-0aabe9bfa712466794b5bc2f0dab23d3
Source dataset
uspto-grants-2000_06
Patent number
US06080754

Reaction notes

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