Hydrochloric Acid → HCID 14724722, compound

HRID 1460719Notes

Reaction equation

HRID 1460719 reaction equation
C(N1CCOCC1)C.C1CCC(N=C=NC2CCCCC2)CC1.[NH:24]([C:36]([O:38][CH2:39][C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1)=[O:37])[C@@H:25]([C:33]([OH:35])=O)[CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.C1C=CC2N(O)N=NC=2C=1.Cl.[NH2:57][C@H:58]([C:65]([O:67][C:68]([CH3:71])([CH3:70])[CH3:69])=[O:66])[CH2:59][O:60][C:61]([CH3:64])([CH3:63])[CH3:62]>CN(C)C=O>[NH:24]([C:36]([O:38][CH2:39][C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1)=[O:37])[C@@H:25]([C:33]([NH:57][C@H:58]([C:65]([O:67][C:68]([CH3:71])([CH3:70])[CH3:69])=[O:66])[CH2:59][O:60][C:61]([CH3:64])([CH3:62])[CH3:63])=[O:35])[CH2:26][C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1

Participants

8

Reactant 6

HCID 313Hydrochloric AcidHCID 7525EthylmorpholineHCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 675678N-(Benzyloxycarbonyl)-D-phenylalanineHCID 6993439(S)-tert-Butyl 2-amino-3-(tert-butoxy)propanoate

Product 1

HCID 14724722HCID 14724722, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

9.07 ml of N-ethylmorpholine and 16.05 g of DCC are added at 0° C. to a solution of 21.2 g of Z-D-Phe-OH, 9.6 g of HOBt and 17.9 g of HCl.H-Ser(tBu)-OtBu in 150 ml of dimethylformamide. The mixture is left to stir at 0° C. for one hour and to stand at room temperature overnight. The precipitate is filtered off with suction, and the filtrate is concentrated. The residue is partitioned between ethyl acetate and water. The ethyl acetate phase is extracted by shaking successively with saturated NaHCO3 solution, KHSO4 /K2SO4 solution and water, dried over Na2SO4 and concentrated. The substance crystallizes after trituration with petroleum ether.

Workup

  1. waitThe mixture is left
  2. waitto stand at room temperature overnight
  3. filtrationThe precipitate is filtered off with suction
  4. concentrationthe filtrate is concentrated
  5. customThe residue is partitioned between ethyl acetate and water
  6. extractionThe ethyl acetate phase is extracted
  7. stirringby shaking successively with saturated NaHCO3 solution, KHSO4 /K2SO4 solution and water
  8. dry with materialdried over Na2SO4
  9. concentrationconcentrated
  10. customThe substance crystallizes after trituration with petroleum ether

Sources & evidence

ORD record
ord-41804773038146aea56c1b0e7d070cff
Source dataset
uspto-grants-1991_12
Patent number
US05071836

Reaction notes

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