N-Dodecylaniline → (R)-benzyl 4-(dimethylamino)-3-(3-dodecyl-3-phenylureido)butanoate

HRID 1958727Notes

Reaction equation

[NH2:1][C@@H:2]([CH2:14][N:15]([CH3:17])[CH3:16])[CH2:3][C:4]([O:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)=[O:5].ClC(Cl)(O[C:22](=[O:28])OC(Cl)(Cl)Cl)Cl.[CH2:30]([NH:42][C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1)[CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH3:41]>>[CH3:17][N:15]([CH3:16])[CH2:14][C@H:2]([NH:1][C:22]([N:42]([CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH3:41])[C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1)=[O:28])[CH2:3][C:4]([O:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)=[O:5]

Participants

Reactant 3

HCID 76362N-Dodecylaniline

HCID 94429Triphosgene

HCID 46223508(R)-benzyl 3-amino-4-(dimethylamino)butanoate

Product 1

HCID 86641224(R)-benzyl 4-(dimethylamino)-3-(3-dodecyl-3-phenylureido)butanoate

Procedure

According to the method described in example S40a, (R)-benzyl 3-amino-4-(dimethylamino)butanoate is reacted with of triphosgene and N-dodecylaniline to yield (R)-benzyl 4-(dimethylamino)-3-(3-dodecyl-3-phenylureido)butanoate. According to the methods described in example S40b,c the preceding benzyl ester is converted to the title compound.

Sources & evidence

ORD record: ord-35357cac0cd24c408c79d5faa4d6547b
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08410150B2

Reaction notes

Loading…