Diethylamine → HCID 68281681, compound

HRID 625141Notes

Reaction equation

HRID 625141 reaction equation
C1C2C(COC(=O)[NH:17][C@H:18]([C:29](=[O:69])[NH:30][C@H:31]([C:58](=[O:68])[NH:59][C:60]3[CH:65]=[CH:64][C:63]([CH2:66][OH:67])=[CH:62][CH:61]=3)[CH2:32][CH2:33][CH2:34][CH2:35][NH:36][C:37]([C:50]3[CH:55]=[CH:54][C:53]([O:56][CH3:57])=[CH:52][CH:51]=3)([C:44]3[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=3)[C:38]3[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=3)[CH2:19][C:20]3[CH:25]=[CH:24][C:23]([N+:26]([O-:28])=[O:27])=[CH:22][CH:21]=3)C3C(=CC=CC=3)C=2C=CC=1.C(NCC)C>C1COCC1>[OH:67][CH2:66][C:63]1[CH:62]=[CH:61][C:60]([NH:59][C:58](=[O:68])[C@@H:31]([NH:30][C:29](=[O:69])[C@@H:18]([NH2:17])[CH2:19][C:20]2[CH:25]=[CH:24][C:23]([N+:26]([O-:28])=[O:27])=[CH:22][CH:21]=2)[CH2:32][CH2:33][CH2:34][CH2:35][NH:36][C:37]([C:50]2[CH:55]=[CH:54][C:53]([O:56][CH3:57])=[CH:52][CH:51]=2)([C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)[C:44]2[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=2)=[CH:65][CH:64]=1

Participants

4

Reactant 2

HCID 8021DiethylamineHCID 86718856HCID 86718856, compound

Product 1

HCID 68281681HCID 68281681, compoundYield 54.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In a 50 mL round-bottomed flask, the above prepared [(S)-1-((S)-1-(4-hydroxymethyl-phenylcarbamoyl)-5-{[(4-methoxy-phenyl)-diphenyl-methyl]-amino}-pentylcarbamoyl)-2-(4-nitro-phenyl)-ethyl]-carbamic acid 9H-fluoren-9-ylmethyl ester (1.214 g, 1.29 mmol, Eq: 1.001) was combined with THF (19 ml) to give a brown solution. At 0°, diethylamine (1.77 g, 2.49 ml, 24.2 mmol, Eq: 18.70) was added. The reaction was stirred at ambient temperature for 3 h when MS indicated the disappearance of the starting material. All volatiles were evaporated i. V.; ensuing flash chromatography SiO2/0.1% NEt3 in CH2Cl2=>10% MeOH/0.1% NEt3 in CH2Cl2, followed by a second flash chromatography SiO2/5% MeOH/0.1% NEt3 in CH2Cl2 afforded 502 mg of the title compound as light brown foam. MS: expected mass: 715.337, found mass: 715.3362.

Workup

  1. customto give a brown solution
  2. customAll volatiles were evaporated i

Sources & evidence

ORD record
ord-5ef49db75e97404482d4cacc6a7738d1
Source dataset
uspto-grants-2016_04
Patent number
US09301990B2

Reaction notes

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