Sodium hydride → HCID 19001939, compound

HRID 2259951Notes

Reaction equation

HRID 2259951 reaction equation
[C:1]1(=[O:34])[N:5]([CH2:6][C:7]([N:9]([CH2:21][C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2OC(F)(F)F)=[O:8])[C:4](=[O:29])[C:3]2=[CH:30][CH:31]=[CH:32][CH:33]=[C:2]12.[CH2:35]([O:37][C:38](C1C=CC=CC=1NC(=O)CN1C(=O)C2=CC=CC=C2C1=O)=[O:39])[CH3:36].[H-].[Na+].BrCC(OC(C)(C)C)=O>>[CH2:35]([O:37][C:38]([C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=1[N:9]([CH2:21][C:22]([O:24][C:25]([CH3:26])([CH3:27])[CH3:28])=[O:23])[C:7](=[O:8])[CH2:6][N:5]1[C:4](=[O:29])[C:3]2=[CH:30][CH:31]=[CH:32][CH:33]=[C:2]2[C:1]1=[O:34])=[O:39])[CH3:36]

Participants

5

Reactant 4

HCID 24758Sodium hydrideHCID 79177tert-Butyl bromoacetateHCID 1370906HCID 1370906, compoundHCID 19001951HCID 19001951, compound

Product 1

HCID 19001939HCID 19001939, compound

Procedure

tert-Butyl 2-[N-(2-ethoxycarbonylphenyl)-2-phthalimidoacetamido] acetate may be prepared in a manner similar to that described in Example 4 for the preparation of tert-butyl 2-[2-phthalimido-N-(2-trifluoromethoxyphenyl)acetamido]acetate, but starting with N-(2-ethoxycarbonylphenyl)-2-phthalimidoacetamide (7.7 g), an oily suspension (50% by weight) (1.26 g) of sodium hydride and tert-butyl bromoacetate (4.3 g). After recrystallisation in diisopropyl ether, tert-butyl 2-[N-(2-ethoxycarbonylphenyl)-2-phthalimidoacetamido]acetate (6.1 g), m.p. 127° C., is thereby obtained.

Workup

  1. customAfter recrystallisation in diisopropyl ether

Sources & evidence

ORD record
ord-6bd4d890a01b4a2eb713f484ee1d67c0
Source dataset
uspto-grants-1995_12
Patent number
US05475106

Reaction notes

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