Vinyl Acetate → HCID 10929006, compound

HRID 1584353Notes

Reaction equation

[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[O:7][C:8]([CH3:32])=[C:9]([CH2:11][O:12][C:13]2[CH:18]=[CH:17][C:16]([CH2:19][CH2:20][CH2:21][CH:22]([OH:29])[C:23]([O:25][CH:26]([CH3:28])[CH3:27])=[O:24])=[CH:15][C:14]=2[O:30][CH3:31])[N:10]=1.[C:33](OC=C)(=[O:35])[CH3:34]>C1(C)C=CC=CC=1>[C:33]([O:29][C@H:22]([CH2:21][CH2:20][CH2:19][C:16]1[CH:17]=[CH:18][C:13]([O:12][CH2:11][C:9]2[N:10]=[C:6]([C:2]3[O:1][CH:5]=[CH:4][CH:3]=3)[O:7][C:8]=2[CH3:32])=[C:14]([O:30][CH3:31])[CH:15]=1)[C:23]([O:25][CH:26]([CH3:27])[CH3:28])=[O:24])(=[O:35])[CH3:34]

Participants

Conditions

Temperature: 23 °C

Procedure

A 3-L flask was successively charged with isopropyl (±)-5-[4-[2-(2-furyl)-5-methyl-4-oxazolylmethoxy]-3-methoxyphenyl]-2-hydroxypentanoate (33.0 g), LIP-301 [immobilized lipase derived from Pseudomonas sp, TOYOBO CO., LTD] (16.5 g), molecular sieve 4A (33 g), toluene (1650 ml) and vinyl acetate (158 ml). The mixture was stirred for 4 hours at 23° C. The reaction mixture was subjected to filtration, and the filtrate was concentrated under reduced pressure. The concentrate was subjected to column chromatography on silica gel. From the fraction eluted with isopropyl ether, was obtained isopropyl (R)-(+)-2-acetoxy-5-[4-[2-(2-furyl)-5-methyl-4-oxazolylmethoxy]-3-methoxyphenyl]pentanoate (15.9 g). Chiral analysis of this compound by HPLC showed 96% ee.

Workup

filtrationThe reaction mixture was subjected to filtration
concentrationthe filtrate was concentrated under reduced pressure
washFrom the fraction eluted with isopropyl ether

Sources & evidence

ORD record: ord-f17c9322ab35411f8c23a551e52f0529
Source dataset: uspto-grants-1999_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05932601

Reaction notes

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