Diethylamine → HCID 86718855, compound

HRID 1498001Notes

Reaction equation

HRID 1498001 reaction equation
C1C2C(COC(=O)[NH:17][C@H:18]([C:26](=[O:44])[NH:27][C@H:28]([C:33](=[O:43])[NH:34][C:35]3[CH:40]=[CH:39][C:38]([CH2:41][OH:42])=[CH:37][CH:36]=3)[CH2:29][CH2:30][CH2:31][CH3:32])[CH2:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)C3C(=CC=CC=3)C=2C=CC=1.C(NCC)C>C(Cl)Cl>[OH:42][CH2:41][C:38]1[CH:37]=[CH:36][C:35]([NH:34][C:33](=[O:43])[C@@H:28]([NH:27][C:26](=[O:44])[C@@H:18]([NH2:17])[CH2:19][C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH2:29][CH2:30][CH2:31][CH3:32])=[CH:40][CH:39]=1

Participants

4

Reactant 2

HCID 8021DiethylamineHCID 86718854HCID 86718854, compound

Product 1

HCID 86718855HCID 86718855, compoundYield 70.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In a round-bottomed flask, the above prepared {(S)-1-[(S)-1-(4-hydroxymethyl-phenylcarbamoyl)-pentylcarbamoyl]-2-phenyl-ethyl}-carbamic acid 9H-fluoren-9-ylmethyl ester (4.738 g, 7.822 mmol, Eq: 1.0) was dissolved in CH2Cl2 (28 ml). At 0°, diethylamine (28 ml, 19.80 g, 271 mmol, Eq: 35) was added and the reaction mixture stirred at ambient temperature over night. All volatiles were evaporated i. V.; ensuing flash chromatography SiO2/CH2Cl2/10% MeOH, followed by crystallization from AcOEt, yielded 2.116 g of the title compound as light brown crystals. MS (ISP): (M+H) 384.2.

Workup

  1. customAll volatiles were evaporated i
  2. customfollowed by crystallization from AcOEt

Sources & evidence

ORD record
ord-2c7bcc72fda44566a0da8030912fbdd0
Source dataset
uspto-grants-2015_12
Patent number
US09198947B2

Reaction notes

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