Hydrochloric Acid → HCID 57152477, compound

HRID 1066572Notes

Reaction equation

HRID 1066572 reaction equation
FC(F)(F)[C:3]([OH:5])=O.[NH2:8][C@@H:9]([CH2:28][C:29](=[O:42])[N:30]1[CH2:35][CH2:34][N:33]([C:36]2[CH:41]=[CH:40][N:39]=[CH:38][CH:37]=2)[CH2:32][CH2:31]1)[C:10]([N:12]1[CH2:17][CH2:16][N:15]([CH2:18][C:19]([OH:21])=[O:20])[C:14](=[O:22])[C@@:13]1([CH:25]=[C:26]=[O:27])OC)=[O:11].[C:43](=O)([O-])O.[Na+].Cl[C:49](OC)=[S:50].Cl>O1CCOCC1.O>[CH3:43][C:49]([NH:8][C@@H:9]([CH2:28][C:29](=[O:42])[N:30]1[CH2:35][CH2:34][N:33]([C:36]2[CH:37]=[CH:38][N:39]=[CH:40][CH:41]=2)[CH2:32][CH2:31]1)[C:10]([N:12]1[CH2:17][CH2:16][N:15]([CH2:18][C:19]([OH:21])=[O:20])[C:14](=[O:22])[C@H:13]1[CH2:25][C:26]([O:5][CH3:3])=[O:27])=[O:11])=[S:50]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 554404Methyl chloromethanethioateHCID 86756995(r,s)-[4-[2-Amino-4-oxo-4-[4-(pyridin-4-yl)piperazin-1-yl]butyryl]-3-methoxy-carbonylmethyl-2-oxopiperazin-1-yl]acetic acid trifluoroacetic acid salt

Product 1

HCID 57152477HCID 57152477, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

To a mixture of (R,S)-[4-[2-amino-4-oxo-4-[4-(pyridin-4-yl)piperazin-1-yl]butyryl]-3-methoxy-carbonylmethyl-2-oxopiperazin-1-yl]acetic acid trifluoroacetic acid salt (0.25 g) produced in Working Example 21, an aqueous solution of sodium hydrogen carbonate (0.15 g), water (2.5 ml) and 1,4-dioxane (2.5 ml)was added methyl chlorothioformate (0.047 ml) and the solution was stirred for 1 hour at room temperature. To the reaction solution was added 1N hydrochloric acid and the solution was adjusted to pH 3, which was concentrated under reduced pressure. The concentrate was purified by CHP-20 column chromatography (eluent:H2O→10% acetonitrile aqueous solution). The objected fraction was concentrated and subjected to lyophilization to give the titled compound (0.18 g) as a white amorphous powdery product.

Workup

  1. customproduced in Working Example 21
  2. concentrationwas concentrated under reduced pressure
  3. customThe concentrate was purified by CHP-20 column chromatography (eluent:H2O→10% acetonitrile aqueous solution)
  4. concentrationThe objected fraction was concentrated

Sources & evidence

ORD record
ord-907faad2b0ff44d189f6e780718697d6
Source dataset
uspto-grants-2001_06
Patent number
US06242600B1

Reaction notes

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