HCID 24773279, compound → HCID 86658808, compound

HRID 2274698Notes

Reaction equation

[CH2:1]([NH:8][C:9](=[O:16])[NH:10][O:11][CH2:12][C:13]([OH:15])=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:17][C@@H:18]([CH2:41][C:42]1[CH:47]=[CH:46][C:45]([O:48][C:49]([CH3:52])([CH3:51])[CH3:50])=[CH:44][CH:43]=1)[C:19]([N:21]([CH2:33][CH:34]([O:38][CH2:39][CH3:40])[O:35][CH2:36][CH3:37])[CH2:22][C:23]1[C:32]2[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=2)[CH:26]=[CH:25][CH:24]=1)=[O:20]>>[CH2:1]([NH:8][C:9](=[O:16])[NH:10][O:11][CH2:12][C:13]([NH:17][C@@H:18]([CH2:41][C:42]1[CH:47]=[CH:46][C:45]([O:48][C:49]([CH3:51])([CH3:50])[CH3:52])=[CH:44][CH:43]=1)[C:19]([N:21]([CH2:33][CH:34]([O:38][CH2:39][CH3:40])[O:35][CH2:36][CH3:37])[CH2:22][C:23]1[C:32]2[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=2)[CH:26]=[CH:25][CH:24]=1)=[O:20])=[O:15])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

Reactant 2

HCID 24773279HCID 24773279, compound

HCID 533974882-((3-Benzylureido)oxy)acetic acid

Product 1

HCID 86658808HCID 86658808, compoundYield 54.5%

Procedure

According to the procedure described in the synthesis method of Compound II-1, 2-(3-benzylureidooxy)acetic acid (Compound VI-6) (247 mg, 1.0 mmol) was coupled with (S)-2-amino-3-(4-tert-butoxyphenyl)-N-(2,2-diethoxyethyl)-N-(naphthalen-1-ylmethyl)propanamide (Compound IV-2) (502 mg, 1.0 mmol) and the obtained residue was purified by silica gel column chromatography (eluent: chloroform:methanol=98:2 to 97:3) to obtain the title compound (381 mg, 52%).

Workup

customthe obtained residue was purified by silica gel column chromatography (eluent: chloroform:methanol=98:2 to 97:3)

Sources & evidence

ORD record: ord-b0351156ef8643c394a9f3dad1cfd6e7
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09126981B2

Reaction notes

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