Dicyclohexylcarbodiimide → HCID 178465152, compound

HRID 1763728Notes

Reaction equation

HRID 1763728 reaction equation
[ClH:1].[CH2:2]([NH:4][C:5](=[O:30])[C@@H:6]1[CH2:10][CH2:9][CH2:8][N:7]1[C:11](=[O:29])[C@H:12]([CH2:22][CH2:23][CH2:24][NH:25][C:26](=[NH:28])[NH2:27])[NH:13][C:14](=[O:21])[C@H:15]([CH2:17][CH:18]([CH3:20])[CH3:19])[NH2:16])[CH3:3].[CH2:31]([O:38][C:39]([NH:41][C@@H:42]([C:50](O)=[O:51])[CH2:43][C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1)=[O:40])[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1.ON1C2C=CC=CC=2N=N1.C1(N=C=NC2CCCCC2)CCCCC1>CN(C)C=O>[ClH:1].[CH2:2]([NH:4][C:5](=[O:30])[C@@H:6]1[CH2:10][CH2:9][CH2:8][N:7]1[C:11](=[O:29])[C@H:12]([CH2:22][CH2:23][CH2:24][NH:25][C:26](=[NH:27])[NH2:28])[NH:13][C:14](=[O:21])[C@H:15]([CH2:17][CH:18]([CH3:19])[CH3:20])[NH:16][C:50](=[O:51])[C@@H:42]([CH2:43][C:44]1[CH:45]=[CH:46][CH:47]=[CH:48][CH:49]=1)[NH:41][C:39]([O:38][CH2:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)=[O:40])[CH3:3]

Participants

6

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 675678N-(Benzyloxycarbonyl)-D-phenylalanineHCID 178465164HCID 178465164, compound

Product 1

HCID 178465152HCID 178465152, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
23 °C

Procedure

A mixture of the above product g), 900 mg. of Nα -benzyloxycarbonyl-D-phenylalanine [cf. Yajima and Kubo, J. Am. Chem. Soc., 87, 2039 (1965)] and 400 mg. of 1-hydroxybenztriazole is dissolved in 40 ml. of dimethylformamide and then cooled and treated with 700 mg. of dicyclohexylcarbodiimide. The reaction is stirred at 23° C. for three days, filtered and the filtrate evaporated at 50° C. and under reduced pressure. The residue is obtained solid by repeated precipitation from methanol by ether and by ethyl acetate and ether; liquifies 130°-135° C.; [α]D23 -69° (c 1.02, methanol); ultraviolet in methanol λmax 258 E11 5.8.

Workup

  1. additiontreated with 700 mg
  2. filtrationfiltered
  3. customthe filtrate evaporated at 50° C. and under reduced pressure
  4. customThe residue is obtained solid
  5. customby repeated precipitation from methanol by ether
  6. customliquifies 130°-135° C.

Sources & evidence

ORD record
ord-238d6f8ba61f4abcbdd58af5062493d1
Source dataset
uspto-grants-1978_09
Patent number
US04111923

Reaction notes

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