(3S,4S)-4-(1-hydroxymethylethenyl)-3-(1-(R)-benzyloxycarbonyloxyethyl)-2-azetidinone → (3S,4S)-4-(1-tetrahydropyranyloxymethylethenyl)-3-(1-(R)-benzyloxycarbonyloxyethyl)-2-azetidinone

HRID 1196208Notes

Reaction equation

HRID 1196208 reaction equation
OCC([C@H]1NC(=O)[C@@H]1[C@H](OC(OCC1C=CC=CC=1)=O)C)=C.[O:23]1[CH2:28][CH2:27][CH2:26][CH2:25][CH:24]1[O:29][CH2:30][C:31]([C@H:33]1[N:36](C2CCCCO2)[C:35](=[O:43])[C@@H:34]1[C@H:44]([O:46][C:47]([O:49][CH2:50][C:51]1[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=1)=[O:48])[CH3:45])=[CH2:32]>>[O:23]1[CH2:28][CH2:27][CH2:26][CH2:25][CH:24]1[O:29][CH2:30][C:31]([C@H:33]1[NH:36][C:35](=[O:43])[C@@H:34]1[C@H:44]([O:46][C:47]([O:49][CH2:50][C:51]1[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=1)=[O:48])[CH3:45])=[CH2:32]

Participants

3

Reactant 2

HCID 15000240(3S,4S)-4-(1-hydroxymethylethenyl)-3-(1-(R)-benzyloxycarbonyloxyethyl)-2-azetidinoneHCID 15000245(3S,4S)-4-(1-tetrahydropyranyloxymethylethenyl)-3-(1-(R)-benzyloxycarbonyloxyethyl)-1-tetrahydropyranyl-2-azetidinone2×

Product 1

HCID 15000244(3S,4S)-4-(1-tetrahydropyranyloxymethylethenyl)-3-(1-(R)-benzyloxycarbonyloxyethyl)-2-azetidinone

Procedure

Following the procedure as described in Example 15-(1) but replacing the starting material by (3S,4S)-4-(1-hydroxymethylethenyl)-3-(1-(R)-benzyloxycarbonyloxyethyl)-2-azetidinone, (3S,4S)-4-(1-tetrahydropyranyloxymethylethenyl)-3-(1-(R)-benzyloxycarbonyloxyethyl)-1-tetrahydropyranyl-2-azetidinone (Compound A) and (3S,4S)-4-(1-tetrahydropyranyloxymethylethenyl)-3-(1-(R)-benzyloxycarbonyloxyethyl)-2-azetidinone (Compound B) were obtained.

Sources & evidence

ORD record
ord-0e21690334f74b1e91484789ad4a163a
Source dataset
uspto-grants-1992_05
Patent number
US05112966

Reaction notes

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