Citric Acid → HCID 70064868, compound

HRID 1110461Notes

Reaction equation

HRID 1110461 reaction equation
C([O:3][C:4](=[O:57])[C@H:5]([CH2:45][C:46]1[CH:51]=[CH:50][C:49]([O:52][C:53]([CH3:56])([CH3:55])[CH3:54])=[CH:48][CH:47]=1)[NH:6][C:7]([C:9]1([CH2:14][CH:15]([C:38]([O:40][C:41]([CH3:44])([CH3:43])[CH3:42])=[O:39])[CH2:16][NH:17][C:18](=[O:37])[C@H:19]([CH2:25][CH2:26][CH2:27][CH2:28][NH:29][C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])[NH:20][S:21]([CH3:24])(=[O:23])=[O:22])[CH2:13][CH2:12][CH2:11][CH2:10]1)=[O:8])C.[OH-].[Na+].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>CC(C)=O>[CH3:24][S:21]([NH:20][C@H:19]([C:18]([NH:17][CH2:16][CH:15]([C:38]([O:40][C:41]([CH3:44])([CH3:43])[CH3:42])=[O:39])[CH2:14][C:9]1([C:7]([NH:6][C@H:5]([C:4]([OH:57])=[O:3])[CH2:45][C:46]2[CH:47]=[CH:48][C:49]([O:52][C:53]([CH3:54])([CH3:55])[CH3:56])=[CH:50][CH:51]=2)=[O:8])[CH2:13][CH2:12][CH2:11][CH2:10]1)=[O:37])[CH2:25][CH2:26][CH2:27][CH2:28][NH:29][C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])(=[O:23])=[O:22]

Participants

5

Reactant 3

HCID 311Citric AcidHCID 14798Sodium HydroxideHCID 131716726HCID 131716726, compound

Product 1

HCID 70064868HCID 70064868, compoundYield 88.5%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

N-{1-[3-(N2 -Methanesulphonyl-N6 -t-butyloxycarbonyl-(S)-lysyl-amino)-2(R,S)-t-butyloxycarbonylpropyl]-1-cyclopentanecarbonyl}-O-t- butyl-(S)-tyrosine ethyl ester (2.21 g, 2.68 mmol) was dissolved in acetone (5.5 ml) and then a 1N aqueous solution of sodium hydroxide (5.36 ml, 5.38 mmol) was added. After stirring for 10 minutes at room temeprature the solution was acidified to pH4 with aqueous citric acid (10%). The acetone was then removed on a rotary evaporator and the residue extracted with ethyl acetate (50 ml). The organic phase was separated, washed with saturated brine, dried over magnesium sulphate and the solvent removed under reduced pressure to yield the title compound as a white foam (1.89 g, 88%). Found: C,58.49; H,8.01; N,6.64. C19H64N4O11S requires C,58.77; H,8.09; N,7.03%.

Workup

  1. customThe acetone was then removed on a rotary evaporator
  2. extractionthe residue extracted with ethyl acetate (50 ml)
  3. customThe organic phase was separated
  4. washwashed with saturated brine
  5. dry with materialdried over magnesium sulphate
  6. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-3c04355fbd3d486c983f68cc092e9cca
Source dataset
uspto-grants-1990_12
Patent number
US04975444

Reaction notes

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