Acetic Anhydride → HCID 53908221, compound

HRID 1107833Notes

Reaction equation

[S:1]([CH:13]1[CH2:18][CH2:17][CH2:16][CH2:15][CH:14]1[NH2:19])[C@@H:2]1[O:10][C@H:9]([CH2:11][OH:12])[C@H:7]([OH:8])[C@H:5]([OH:6])[C@H:3]1[OH:4].[C:20](OC(=O)C)(=[O:22])[CH3:21]>>[S:1]([CH:13]1[CH2:18][CH2:17][CH2:16][CH2:15][CH:14]1[NH:19][C:20](=[O:22])[CH3:21])[C@@H:2]1[O:10][C@H:9]([CH2:11][OH:12])[C@H:7]([OH:8])[C@H:5]([OH:6])[C@H:3]1[OH:4]

Participants

Reactant 2

HCID 7918Acetic Anhydride

HCID 18392971HCID 18392971, compound

Product 1

HCID 53908221HCID 53908221, compound

Procedure

Alternatively, compound 9 is reductively aminated with ammonium acetate and sodium cyanoborohydride to provide for intermediate 11 which, upon removal of the lauroyl groups, affords 2-aminocyclohexyl 1-thio-β-D-galactopyranoside, B2. Compound B2 can then be acylated with acetic anhydride to give 2-acetamidocyclohexyl 1-thio-β-D-galactopyranoside, C2. Alternatively, intermediate 11 can be acylated with phthalic anhydride to provide for intermediate 12 which affords 2-(2-carboxybenzamidocyclohexyl 1-thio-β-D-galactopyranoside, D2, by removal of the lauroyl groups using the conditions described above.

Sources & evidence

ORD record: ord-6d8a97bc35c74d55a56f2361bdf7548e
Source dataset: uspto-grants-2000_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06063769

Reaction notes

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