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 899490Notes

Reaction equation

HRID 899490 reaction equation
B(O)O.O[C:5](C(O)(C)C)([CH3:7])[CH3:6].C(B1OC(C)(C)C(C)(C)O1)C=C.[CH:24]([C:26]1[C@H:31]([C:32]([O:34][CH:35]([C:42]2[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=2)[C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)=[O:33])[N:30]2[C:48](=[O:60])[C@@H:49]([NH:50][C:51](=[O:59])[CH2:52][C:53]3[CH:58]=[CH:57][CH:56]=[CH:55][CH:54]=3)[C@H:29]2[S:28][CH:27]=1)=[O:25]>C1(C)C=CC=CC=1>[OH:25][CH:24]([C:26]1[C@H:31]([C:32]([O:34][CH:35]([C:36]2[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=2)[C:42]2[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=2)=[O:33])[N:30]2[C:48](=[O:60])[C@@H:49]([NH:50][C:51](=[O:59])[CH2:52][C:53]3[CH:54]=[CH:55][CH:56]=[CH:57][CH:58]=3)[C@H:29]2[S:28][CH:27]=1)[CH2:7][CH:5]=[CH2:6]

Participants

5

Reactant 3

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 esterHCID 178459139HCID 178459139, compound

Product 1

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

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

via a pinacol boronate. 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-2a944592fbc9427d9367312d6bc3bbcd
Source dataset
uspto-grants-2008_04
Patent number
US07355040B2

Reaction notes

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