Dicyclohexylcarbodiimide → benzyl-2-(N-FMOC-L-valyloxy)stearate

HRID 489075

Reaction equation

HRID 489075 reaction equation
[CH2:1]([O:8][C:9](=[O:28])[CH:10]([OH:27])[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:29]([NH:46][C@H:47]([C:51](O)=[O:52])[CH:48]([CH3:50])[CH3:49])([O:31][CH2:32][CH:33]1[C:45]2[C:40](=[CH:41][CH:42]=[CH:43][CH:44]=2)[C:39]2[C:34]1=[CH:35][CH:36]=[CH:37][CH:38]=2)=[O:30].C1CCC(N=C=NC2CCCCC2)CC1>CN(C1C=CN=CC=1)C.ClCCl>[CH2:1]([O:8][C:9](=[O:28])[CH:10]([O:27][C:51](=[O:52])[C@H:47]([CH:48]([CH3:49])[CH3:50])[NH:46][C:29]([O:31][CH2:32][CH:33]1[C:34]2[C:39](=[CH:38][CH:37]=[CH:36][CH:35]=2)[C:40]2[C:45]1=[CH:44][CH:43]=[CH:42][CH:41]=2)=[O:30])[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 688217FMOC-L-valineHCID 22035791Benzyl 2-hydroxystearate

Product 1

HCID 23387558benzyl-2-(N-FMOC-L-valyloxy)stearate

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of benzyl-2-hydroxystearate (3.2 g, 8.2 mmole), N-FMOC-L-valine (3.4 g, 10 mmole) and DMAP (0.12 g, 1 mmole) in 80 ml dichloromethane was added a solution of DCC (2.5 g, 12 mmole) and the mixture was stirred overnight at room temperature. The mixture was cooled to 5° C. and the urethane was filtered. The filtrate was evaporated and the product was isolated by silica gel column chromatography. Yield: 4.5 g

Workup

  1. temperatureThe mixture was cooled to 5° C.
  2. filtrationthe urethane was filtered
  3. customThe filtrate was evaporated
  4. customthe product was isolated by silica gel column chromatography

Sources & evidence

ORD record
ord-55e6eab99dea4777903a31eabdd16b09
Source dataset
uspto-grants-2005_12
Patent number
US06974802B2

Linked notes

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