Acetonitrile--water (1/1) → 17-(tert-Butoxy)-17-oxoheptadecanoic acid

HRID 562521Notes

Reaction equation

HRID 562521 reaction equation
O=C1CCC(=O)N1OC(=O)C1C=CC(CN(CCC(OC(C)(C)C)=O)[C:18](=[O:41])[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][C:34]([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:35])=CC=1.C(#N)C.[OH2:55]>>[C:37]([O:36][C:34](=[O:35])[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29][CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][C:18]([OH:41])=[O:55])([CH3:38])([CH3:39])[CH3:40]

Participants

3

Reactant 2

HCID 18373917Acetonitrile--water (1/1)HCID 580794734-{[(2-tert-Butoxycarbonylethyl)-(16-tert-butoxycarbonylhexadecanoyl)-amino]methyl}benzoic acid 2,5-dioxopyrrolidin-1-yl ester

Product 1

HCID 5807948617-(tert-Butoxy)-17-oxoheptadecanoic acid

Procedure

4-{[(2-tert-Butoxycarbonylethyl)-(16-tert-butoxycarbonylhexadecanoyl)-amino]methyl}benzoic acid 2,5-dioxopyrrolidin-1-yl ester was reacted with A1,B1-diBoc desB30 insulin as described in general procedure B. The work up was similar using a gradient 28-48% acetonitrile/water containing 0.1% TFA.

Sources & evidence

ORD record
ord-2c97e6c8badb4d70adadfa48889a1b38
Source dataset
uspto-grants-2011_11
Patent number
US08067362B2

Reaction notes

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