Isobutyric anhydride → HCID 86585445, compound

HRID 1368829Notes

Reaction equation

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

Participants

Reactant 3

HCID 7346Isobutyric anhydride

HCID 18840Cyclopentanecarboxylic acid

HCID 59069980HCID 59069980, compound

Product 1

HCID 86585445HCID 86585445, compound

Procedure

Compound 17 was prepared in the manner of compound 15 utilizing cyclopentanecarboxylic acid under conditions B for introduction of the ester group at the 5′ hydroxyl group, and isobutyric anhydride under conditions A for the introduction of the 2′ and 3′ hydroxyl groups: 1H NMR(CDCl3) δ1.05-1.23 (m, 12H), 1.52-2.05 (m, 8H), 2.26-2.38 (m,1H), 2.49-2.63(m,2H), 2.71-2.79 (m, 1H), 3.75-3.87(m,2H), 3.94-4.06(m,2H), 4.34-4.45 (m, 3H), 4.78-4.86(m, 1H), 5.58 (dd, 1H), 5.81 (dd, 1H), 6.17 (d, 1H), 6.95 (br s, 1H), 7.97 (s,1H), 8.37(s,1H).

Sources & evidence

ORD record: ord-3d4de9951c9a46f9a3c5b0c2f04b6566
Source dataset: uspto-grants-2003_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06576619B2

Reaction notes

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