Citric Acid → HCID 178462265, compound

HRID 544351Notes

Reaction equation

HRID 544351 reaction equation
[NH:1]1[CH2:19][CH2:18][CH2:17][C@H:2]1[C:3]([NH:5][C@H:6]([C:14]([OH:16])=[O:15])[CH2:7][CH2:8][CH2:9][NH:10][C:11](=[NH:13])[NH2:12])=[O:4].[NH:20]([C:35]([O:37][C:38]([CH3:41])([CH3:40])[CH3:39])=[O:36])[C@@H:21]([C:32](O)=[O:33])[C@H:22]([CH3:31])[O:23][CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>CN(C=O)C>[NH:20]([C:35]([O:37][C:38]([CH3:39])([CH3:41])[CH3:40])=[O:36])[C@@H:21]([C:32]([N:1]1[CH2:19][CH2:18][CH2:17][C@H:2]1[C:3]([NH:5][C@H:6]([C:14]([OH:16])=[O:15])[CH2:7][CH2:8][CH2:9][NH:10][C:11](=[NH:12])[NH2:13])=[O:4])=[O:33])[C@H:22]([CH3:31])[O:23][CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

5

Reactant 3

HCID 311Citric AcidHCID 6992573(2R,3S)-3-(benzyloxy)-2-{[(tert-butoxy)carbonyl]amino}butanoic acidHCID 178512874HCID 178512874, compound

Product 1

HCID 178462265HCID 178462265, compoundYield 72.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

0.959 g (2.0 mmole) of the 2HCl.H-Pro-Arg-CHA was dissolved in 8 ml of 0.75N NEM/DMF, to which was added 0.863 g (2.0 mmole) of BOC-D-Thr(OBzl)-SDP at0°-5° C., and the reaction was effected at room temperature for 18 hours, after which the reaction mixture was poured into 2000 ml of cold 1/1 solution of 10% citric acid/sat. aqueous Nacl. The precipitate was filtered out and dried, to obtain 1.07 g (72.7%) of BOC-D-Thr(OBzl)-Pro-Arg-CHA.

Workup

  1. filtrationThe precipitate was filtered out
  2. customdried

Sources & evidence

ORD record
ord-4260b21f8b2a4eff8d1369adf9f2d872
Source dataset
uspto-grants-1984_05
Patent number
US04450105

Reaction notes

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