Acetic Anhydride → HCID 178455041, compound

HRID 516895Notes

Reaction equation

[Si:1]([O:8][C:9]1[CH:38]=[CH:37][C:12]([CH2:13][CH:14]([C:34]([OH:36])=O)[C:15]([C@H:20]2[CH2:25][CH2:24][C@@H:23]([O:26][Si:27]([C:30]([CH3:33])([CH3:32])[CH3:31])([CH3:29])[CH3:28])[CH2:22][CH2:21]2)(O)C(O)=O)=[CH:11][CH:10]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[C:39]([O:42]C(=O)C)(=[O:41])C>>[Si:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([CH2:13][C:14]2[C:34](=[O:36])[O:42][C:39](=[O:41])[C:15]=2[C@H:20]2[CH2:25][CH2:24][C@@H:23]([O:26][Si:27]([C:30]([CH3:32])([CH3:31])[CH3:33])([CH3:29])[CH3:28])[CH2:22][CH2:21]2)=[CH:37][CH:38]=1)([C:4]([CH3:6])([CH3:7])[CH3:5])([CH3:3])[CH3:2]

Participants

Reactant 2

HCID 7918Acetic Anhydride

HCID 178455044HCID 178455044, compound

Product 1

HCID 178455041HCID 178455041, compoundYield 70%

Conditions

Temperature: 120 °C

Procedure

3-(4-((tert-Butyldimethylsilyl)oxy)benzyl)-2-(cis-4-((tert-butyldimethylsilyl)oxy)cyclohexyl)-2-hydroxysuccinic acid (90 mg, 0.16 mmol) was dissolved in acetic anhydride (2.0 ml), and the mixture was stirred at 120° C. for 18 hr. The mixture was allowed to cool, excess acetic anhydride was concentrated under reduced pressure, and the residue was chromatographed on silica gel column (hexane:ethyl acetate=94:6) to give the title compound as a yellow oil (60 mg, yield 70%).

Workup

temperatureto cool
concentrationexcess acetic anhydride was concentrated under reduced pressure
customthe residue was chromatographed on silica gel column (hexane:ethyl acetate=94:6)

Sources & evidence

ORD record: ord-ac337ef849fd4b08a2a0e57b3ed6d24a
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09115079B2

Reaction notes

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