4,4,5,5-Tetramethyl-2-(prop-2-en-1-yl)-1,3,2-dioxaborolane → Diphenylmethyl (4R, 6R, 7R)-3(1-hydroxybut 3enyl)7phenylacetamidoceph-2em-4carboxylate

HRID 2417152Notes

Reaction equation

HRID 2417152 reaction equation
[CH2:1](B1OC(C)(C)C(C)(C)O1)[CH:2]=[CH2:3].[CH:13]([C:15]1[C@H:20]([C:21]([O:23][CH:24]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[O:22])[N:19]2[C:37](=[O:49])[C@@H:38]([NH:39][C:40](=[O:48])[CH2:41][C:42]3[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=3)[C@H:18]2[S:17][CH:16]=1)=[O:14]>C1(C)C=CC=CC=1>[OH:14][CH:13]([C:15]1[C@H:20]([C:21]([O:23][CH:24]([C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)[C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)=[O:22])[N:19]2[C:37](=[O:49])[C@@H:38]([NH:39][C:40](=[O:48])[CH2:41][C:42]3[CH:43]=[CH:44][CH:45]=[CH:46][CH:47]=3)[C@H:18]2[S:17][CH:16]=1)[CH2:3][CH:2]=[CH2:1]

Participants

4

Reactant 2

HCID 27631714,4,5,5-Tetramethyl-2-(prop-2-en-1-yl)-1,3,2-dioxaborolaneHCID 113527753-Formyl-7betaphenylacetylamino-ceph-2-em-4alpha-carboxylic acid diphenylmethyl ester

Product 1

HCID 131724666Diphenylmethyl (4R, 6R, 7R)-3(1-hydroxybut 3enyl)7phenylacetamidoceph-2em-4carboxylate

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 2-allyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (50 mg, 0.3 mmol), diphenylmethyl (4R, 6R, 7R)-3-formyl-7-phenylacetamidoceph-2-em-4-carboxylate (100 mg, 0.2 mmol), 0.4 nm molecular sieves (50 mg), and toluene (2 ml) was heated under reflux for 3 h and then cooled and purified by chromatography as in part a to give the title compound S-diastereomer, 20 mg (18%), and the R-diastereomer, 23 mg (20%).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 3 h
  3. temperaturecooled
  4. custompurified by chromatography as in part

Sources & evidence

ORD record
ord-be38d7f06ab34e7fb3f3968208833878
Source dataset
uspto-grants-2004_11
Patent number
US06825344B2

Reaction notes

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