Formic acid--water (1/1) → HCID 45376632, compound

HRID 2274701Notes

Reaction equation

HRID 2274701 reaction equation
[CH2:1]([NH:8][C:9](=[O:53])[NH:10][CH2:11][C:12]1([C:15]([NH:17][C@@H:18]([CH2:41][C:42]2[CH:47]=[CH:46]C(OC(C)(C)C)=[CH:44][CH:43]=2)[C:19]([N:21]([CH2:33][CH:34](OCC)OCC)[CH2:22][C:23]2[C:32]3[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=3)[CH:26]=[CH:25][CH:24]=2)=[O:20])=[O:16])[CH2:14][CH2:13]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:54]([OH:56])=O.O>>[CH2:1]([NH:8][C:9]([N:10]1[CH2:11][C:12]2([CH2:14][CH2:13]2)[C:15](=[O:16])[N:17]2[CH:18]([CH2:41][C:42]3[CH:43]=[CH:44][C:54]([OH:56])=[CH:46][CH:47]=3)[C:19](=[O:20])[N:21]([CH2:22][C:23]3[C:32]4[C:31](=[CH:30][CH:29]=[CH:28][CH:27]=4)[CH:26]=[CH:25][CH:24]=3)[CH2:33][CH:34]12)=[O:53])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 18673298Formic acid--water (1/1)HCID 45377867HCID 45377867, compound

Product 1

HCID 45376632HCID 45376632, compoundYield 29%

Procedure

To (S)-1-((3-benzylureido)methyl)-N-(3-(4-tert-butoxyphenyl)-1-((2,2-diethoxyethyl)(naphthalen-1-ylmethyl)amino)-1-oxopropan-2-yl)cyclopropanecarboxamide (Compound II-1) (188 mg, 0.26 mmol) was added 10%-HCOOH/water (2.0 ml) and the mixture was stirred at room temperature overnight. The reaction mixture was concentrated in vacuo and the residue was purified by silica gel column chromatography (eluent: chloroform:methanol=100:0 to 90:10) to obtain the title compound (47 mg, 29%).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customthe residue was purified by silica gel column chromatography (eluent: chloroform:methanol=100:0 to 90:10)

Sources & evidence

ORD record
ord-b6f761d225374ee7bcd12390b2e881b4
Source dataset
uspto-grants-2015_09
Patent number
US09126981B2

Reaction notes

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