Diethylamine → Benzyl (2-amino-1-{2-(4-chlorophenyl)-1-[(2,2-diethoxyethyl)isopropylcarbamoyl]ethylcarbamoyl}ethyl)carbamate

HRID 1994404Notes

Reaction equation

C1C2C(COC(=O)[NH:17][CH2:18][CH:19]([NH:46][C:47]([O:49][CH2:50][C:51]3[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=3)=[O:48])[C:20](=[O:45])[NH:21][CH:22]([C:31](=[O:44])[N:32]([CH2:36][CH:37]([O:41][CH2:42][CH3:43])[O:38][CH2:39][CH3:40])[CH:33]([CH3:35])[CH3:34])[CH2:23][C:24]3[CH:29]=[CH:28][C:27]([Cl:30])=[CH:26][CH:25]=3)C3C(=CC=CC=3)C=2C=CC=1.C(NCC)C>>[CH2:50]([O:49][C:47](=[O:48])[NH:46][CH:19]([C:20](=[O:45])[NH:21][CH:22]([C:31](=[O:44])[N:32]([CH2:36][CH:37]([O:38][CH2:39][CH3:40])[O:41][CH2:42][CH3:43])[CH:33]([CH3:35])[CH3:34])[CH2:23][C:24]1[CH:25]=[CH:26][C:27]([Cl:30])=[CH:28][CH:29]=1)[CH2:18][NH2:17])[C:51]1[CH:52]=[CH:53][CH:54]=[CH:55][CH:56]=1

Participants

Reactant 2

HCID 8021Diethylamine

HCID 691919629H-fluoren-9-ylmethyl (2-benzyloxycarbonylamino-2-{2-(4-chlorophenyl)-1-[(2,2-diethoxyethyl)isopropylcarbamoyl]ethylcarbamoyl}ethyl)carbamate

Product 1

HCID 86761390Benzyl (2-amino-1-{2-(4-chlorophenyl)-1-[(2,2-diethoxyethyl)isopropylcarbamoyl]ethylcarbamoyl}ethyl)carbamate

Procedure

The Fmoc protective group was eliminated from 9H-fluoren-9-ylmethyl(2-benzyloxycarbonylamino-2-{2-(4-chlorophenyl)-1-[(2,2-diethoxyethyl)isopropylcarbamoyl]ethylcarbamoyl}ethyl)carbamate using diethylamine and employing the method as described under b). The desired product is obtained with MW=576.27 (calculated, monoisotopic); measured value (M+H)+=577.22

Sources & evidence

ORD record: ord-bc06217201d44190a5744231900455aa
Source dataset: uspto-grants-2010_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07652007B2

Reaction notes

Loading…