Dicyclohexylcarbodiimide → HCID 131714718, compound

HRID 1982300Notes

Reaction equation

HRID 1982300 reaction equation
[NH:1]([C:21]([O:23][CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)=[O:22])[C@H:2]([C:6]([NH:8][C@H:9]([C:18](O)=[O:19])[CH2:10][C:11]1[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][CH:12]=1)=[O:7])[CH:3]([CH3:5])[CH3:4].C1C=CC2N(O)N=NC=2C=1.[NH2:41][C@H:42]([C:55]([O:57][CH3:58])=[O:56])[CH2:43][CH2:44][CH2:45][CH2:46][NH:47][C:48]([O:50][C:51]([CH3:54])([CH3:53])[CH3:52])=[O:49].C1CCC(N=C=NC2CCCCC2)CC1>CN(C=O)C.O>[NH:1]([C:21]([O:23][CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)=[O:22])[C@H:2]([C:6]([NH:8][C@H:9]([C:18]([NH:41][C@H:42]([C:55]([O:57][CH3:58])=[O:56])[CH2:43][CH2:44][CH2:45][CH2:46][NH:47][C:48]([O:50][C:51]([CH3:53])([CH3:52])[CH3:54])=[O:49])=[O:19])[CH2:10][C:11]1[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][CH:12]=1)=[O:7])[CH:3]([CH3:5])[CH3:4]

Participants

7

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 7015203Z-Val-Tyr-OHHCID 7018776(S)-Methyl 2-amino-6-((tert-butoxycarbonyl)amino)hexanoate

Product 1

HCID 131714718HCID 131714718, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Procedure

13.8 g of Z-Val-Tyr-OH [R. Schwyzer et al., Helv. Chim. acta. 41, 1273 (1958)] and 5.1 g of HOBt×H2O are dissolved in 100 ml of DMF and there is added thereto the above solution of H-Lys(Boc)-OMe in a small amount of DMF. The whole is cooled to 0°, 7.6 g of DCCI are added and the whole is stirred for 6 hours at 0° and for 10 hours at room temperature. The DCH which has separated out is filtered off and the filtrate is concentrated to dryness. Purification is carried out by triturating with diisopropyl ether and by dissolving and reprecipitating from trifluoroethanol/ethyl acetate/petroleum ether, yielding Z-Val-Tyr-Lys(Boc)-OMe; Rf (F)=0.39.

Workup

  1. additionthere is added
  2. temperatureThe whole is cooled to 0°
  3. customThe DCH which has separated out
  4. filtrationis filtered off
  5. concentrationthe filtrate is concentrated to dryness
  6. customPurification
  7. customby triturating with diisopropyl ether
  8. dissolutionby dissolving
  9. customreprecipitating from trifluoroethanol/ethyl acetate/petroleum ether

Sources & evidence

ORD record
ord-b1d69b1ae4774143b27710c1ba13476e
Source dataset
uspto-grants-1986_06
Patent number
US04595677

Reaction notes

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