tert-Butanol → HCID 131711476, compound

HRID 127462Notes

Reaction equation

HRID 127462 reaction equation
CO/C(/C)=C\C(Cl)=O.S1C2C=CC=CC=2N=C1S[S:19][CH:20]1[N:23](/[C:24](=[C:28](\[O:30][CH3:31])/[CH3:29])/[C:25](Cl)=[O:26])[C:22](=[O:32])[CH:21]1[NH:33][C:34](=[O:43])[CH2:35][O:36][C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1.C(N(CC)CC)C.[C:51]([OH:55])([CH3:54])([CH3:53])[CH3:52]>C(Cl)Cl>[C:51]([O:55][C:25]([CH:24]1[N:23]2[C:22](=[O:32])[C@@H:21]([NH:33][C:34](=[O:43])[CH2:35][O:36][C:37]3[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=3)[C@H:20]2[S:19][CH:29]=[C:28]1[O:30][CH3:31])=[O:26])([CH3:54])([CH3:53])[CH3:52]

Participants

6

Reactant 4

HCID 6386tert-ButanolHCID 8471TriethylamineHCID 14197971HCID 14197971, compoundHCID 887579152-[4-(Benzthiazol-2-yldithio)-3-phenoxyacetamido-2-oxoazetidin-1-yl]-3-methoxy-isocrotonic acid chloride

Product 1

HCID 131711476HCID 131711476, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

A solution of 266 mg (0.5 mM) of a crude mixture consisting of 2-[4-benzthiazol-2-yldithio)-3-phenoxyacetamido-2-oxoazetidin-1-yl]-3-methoxy-crotonic acid chloride and 2-[4-(benzthiazol-2-yldithio)-3-phenoxyacetamido-2-oxoazetidin-1-yl]-3-methoxy-isocrotonic acid chloride in 5 ml of dry methylene chloride is added dropwise over the course of 15 minutes at 0° C., whilst stirring, to a solution of 0.10 ml of triethylamine in 0.5 ml of dry tert.-butanol and 3 ml of methylene chloride. After a further 15 minutes stirring, the reaction mixture is diluted with methylene chloride, washed with water, with dilute hydrochloric acid and again with water, dried over sodium sulphate and concentrated by evaporation in vacuo. The residue is chromatographed on 10 g of acid-washed silica gel, using toluene/ethyl acetate (4:1) as the running agent. 7β-Phenoxyacetamido-3-methoxy-ceph-2-em-4-carboxylic acid tert.butyl ester is obtained. IR spectrum (in CH2Cl2): characteristic bands at 5.60, 5.77, 5.90 and 8.29μ.

Workup

  1. additionis added dropwise over the course of 15 minutes at 0° C.
  2. washwashed with water, with dilute hydrochloric acid and again with water
  3. dry with materialdried over sodium sulphate
  4. concentrationconcentrated by evaporation in vacuo
  5. customThe residue is chromatographed on 10 g of acid-washed silica gel

Sources & evidence

ORD record
ord-47790c3239e44a03b3027f651ee3603d
Source dataset
uspto-grants-1981_03
Patent number
US04255328

Reaction notes

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