Iodomethyl pivalate → HCID 141559409, compound

HRID 1729566Notes

Reaction equation

HRID 1729566 reaction equation
[NH2:1][C:2]1[S:3][CH:4]=[C:5](/[C:7](=[N:29]/[O:30]C(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)/[C:8]([NH:10][CH:11]2[C:27](=[O:28])[N:13]3[C:14]([C:24]([O-:26])=[S:25])=[C:15]([CH2:18][CH:19]4[CH2:23][O:22][CH2:21][O:20]4)[CH2:16][S:17][C@H:12]23)=[O:9])[N:6]=1.[Na+].[C:51]([O:57][CH2:58]I)(=[O:56])[C:52]([CH3:55])([CH3:54])[CH3:53]>>[NH2:1][C:2]1[S:3][CH:4]=[C:5](/[C:7](=[N:29]/[OH:30])/[C:8]([NH:10][CH:11]2[C:27](=[O:28])[N:13]3[C:14]([C:24]([O:26][CH2:58][O:57][C:51](=[O:56])[C:52]([CH3:55])([CH3:54])[CH3:53])=[S:25])=[C:15]([CH2:18][CH:19]4[CH2:23][O:22][CH2:21][O:20]4)[CH2:16][S:17][C@H:12]23)=[O:9])[N:6]=1

Participants

3

Reactant 2

HCID 104401Iodomethyl pivalateHCID 141573508HCID 141573508, compound

Product 1

HCID 141559409HCID 141559409, compoundYield 76.1%

Procedure

Sodium 7-[(Z)-2-(2-aminothiazol-4-yl)-2-trityloxyiminoacetamido]-3-(1,3-dioxolan-4-yl)methylthio-3-cephem-4-carboxylate (71 mg) as prepared in Example 35(b) was reacted with iodomethyl pivalate (68 mg) similarly to Example 28 for the esterification reaction. The resulting reaction solution was post-treated and the produced compound was recovered and purified similarly to Example 28 to give the titled compound (43 mg; 51%).

Workup

  1. customThe resulting reaction solution
  2. additionwas post-treated
  3. customthe produced compound was recovered
  4. custompurified similarly to Example 28

Sources & evidence

ORD record
ord-d7d515c73985475890761f288351c6f9
Source dataset
uspto-grants-1994_07
Patent number
US05332731

Reaction notes

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