Hydrochloric Acid → HCID 67155307, compound

HRID 389657Notes

Reaction equation

HRID 389657 reaction equation
C([O:3][C:4]([CH:6]1[CH2:11][CH2:10][N:9]([C:12](=[O:45])[C@@H:13]([NH:24][S:25]([C:28]2[CH:33]=[CH:32][CH:31]=[C:30]([N:34]3[CH2:39][CH2:38][CH2:37][CH2:36][C:35]3=[O:40])[C:29]=2[O:41][CH:42]([F:44])[F:43])(=[O:27])=[O:26])[CH2:14][NH:15][C:16]([C:18]2[S:19][C:20]([Cl:23])=[CH:21][CH:22]=2)=[O:17])[CH2:8][CH2:7]1)=[O:5])C.[Li+].[OH-].Cl>C1COCC1.C(O)C.O.O>[Cl:23][C:20]1[S:19][C:18]([C:16]([NH:15][CH2:14][C@H:13]([NH:24][S:25]([C:28]2[CH:33]=[CH:32][CH:31]=[C:30]([N:34]3[CH2:39][CH2:38][CH2:37][CH2:36][C:35]3=[O:40])[C:29]=2[O:41][CH:42]([F:44])[F:43])(=[O:26])=[O:27])[C:12]([N:9]2[CH2:8][CH2:7][CH:6]([C:4]([OH:5])=[O:3])[CH2:11][CH2:10]2)=[O:45])=[O:17])=[CH:22][CH:21]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 67155380HCID 67155380, compound

Product 1

HCID 67155307HCID 67155307, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 18504229Ethanol tetrahydrofuran waterSolvent

Procedure

The ethyl ester (1-{(S)-3-[(5-Chloro-thiophene-2-carbonyl)-amino]-2-[2-difluoromethoxy-3-(2-oxo-piperidin-1-yl)-benzenesulfonylamino]-propionyl}-piperidine-4-carboxylic acid ethyl ester) from example 9 (128 mg, 0.185 mmol) was treated with LiOH (222 μl, 0.555 mmol, 2.5 N in water) in THF/ethanol/water (2 ml, 1 ml, 0.5 ml). After 2.5 h the reaction was brought to pH=1-2 using 2 N HCl and further diluted with 30 ml water. The product crystallized from the aq layer and can be separated by filtration. Yield: 54 mg, 44%, colorless crystals.

Workup

  1. customThe product crystallized from the aq layer
  2. customcan be separated by filtration

Sources & evidence

ORD record
ord-1a66422eaa40480bb05e32d32bb036df
Source dataset
uspto-grants-2013_02
Patent number
US08378092B2

Reaction notes

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