Dicyclohexylcarbodiimide → Nalpha-Benzyloxycarbonyl-L-glutaminyl-L-tryptophyl-L-seryl-L-tyrosine methyl ester

HRID 2083823Notes

Reaction equation

HRID 2083823 reaction equation
Cl.[CH3:2][O:3][C:4](=[O:35])[C@H:5]([CH2:27][C:28]1[CH:33]=[CH:32][C:31]([OH:34])=[CH:30][CH:29]=1)[NH:6][C:7](=[O:26])[C@H:8]([CH2:24][OH:25])[NH:9][C:10](=[O:23])[C@H:11]([CH2:13][C:14]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[NH:16][CH:15]=1)[NH2:12].[CH2:36]([O:43][C:44]([NH:46][C@H:47]([C:53](O)=[O:54])[CH2:48][CH2:49][C:50](=[O:52])[NH2:51])=[O:45])[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1.ON1C2C=CC=CC=2N=N1.C1(N=C=NC2CCCCC2)CCCCC1>C(N(CC)CC)C.CN(C)C=O>[CH3:2][O:3][C:4](=[O:35])[C@H:5]([CH2:27][C:28]1[CH:29]=[CH:30][C:31]([OH:34])=[CH:32][CH:33]=1)[NH:6][C:7](=[O:26])[C@H:8]([CH2:24][OH:25])[NH:9][C:10](=[O:23])[C@H:11]([CH2:13][C:14]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[NH:16][CH:15]=1)[NH:12][C:53](=[O:54])[C@H:47]([CH2:48][CH2:49][C:50](=[O:52])[NH2:51])[NH:46][C:44]([O:43][CH2:36][C:37]1[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=1)=[O:45]

Participants

7

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 75855L-Glutamine, N2-[(phenylmethoxy)carbonyl]-HCID 70617527L-tryptophyl-L-seryl-L-tyrosine methyl ester hydrochloride

Product 1

HCID 53973654Nalpha-Benzyloxycarbonyl-L-glutaminyl-L-tryptophyl-L-seryl-L-tyrosine methyl ester

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Conditions

Temperature
-10 °C

Procedure

A mixture of the product from (c) above, 1.4 g. of Nα -benzyloxycarbonyl-L-glutamine, 670 mg. of 1-hydroxybenztriazole and 50 ml. of dimethylformamide is stirred and cooled to -10° C., and 0.7 ml. of triethylamine is added. After 15 minutes, it is treated with 1.2 g. of dicyclohexylcarbodiimide and stirred a few hours at -10° C., then at room temperature for two days and finally let stand an additional three days. The solution is filtered and the filtrate evaporated at 50° C. under reduced pressure. The residue is precipitated from methanol with water and then crystallized from methanol three times; m.p. 245°-248° C.; [α]D25 -4.4° (c 1, DMF); ultraviolet in methanol, λmax 290 E11 75.7; λmax 280 E11 100.

Workup

  1. additionit is treated with 1.2 g
  2. waitat room temperature for two days
  3. waitfinally let stand an additional three days
  4. filtrationThe solution is filtered
  5. customthe filtrate evaporated at 50° C. under reduced pressure
  6. customThe residue is precipitated from methanol with water
  7. customcrystallized from methanol three times

Sources & evidence

ORD record
ord-ddd9ad7cfed644d39542255c8de39518
Source dataset
uspto-grants-1978_04
Patent number
US04086219

Reaction notes

Loading…