Sodium Hydroxide → HCID 178522639, compound

HRID 1035741Notes

Reaction equation

HRID 1035741 reaction equation
[CH:1]1([NH:6][C:7]2[S:11][C:10]([NH:12][C:13]([C:15]3[CH:31]=[CH:30][C:18]([O:19][C@@H:20]4[CH2:25][CH2:24][C@H:23]([C:26]([O:28]C)=[O:27])[CH2:22][CH2:21]4)=[CH:17][CH:16]=3)=[O:14])=[N:9][N:8]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.[OH-].[Na+]>O1CCCC1.CO.O>[CH:1]1([NH:6][C:7]2[S:11][C:10]([NH:12][C:13]([C:15]3[CH:31]=[CH:30][C:18]([O:19][C@@H:20]4[CH2:25][CH2:24][C@H:23]([C:26]([OH:28])=[O:27])[CH2:22][CH2:21]4)=[CH:17][CH:16]=3)=[O:14])=[N:9][N:8]=2)[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 178501270HCID 178501270, compound

Product 1

HCID 178522639HCID 178522639, compoundYield 0.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 21899815MeOH tetrahydrofuranSolvent

Procedure

0.310 g of methyl cis-4-[4-(5-cyclopentylamino[1.3.4]thiadiazol-2-ylcarbamoyl)-phenoxy]cyclohexanecarboxylate (0.70 mmol, 1 eq.) is placed in 8 mL of a tetrahydrofuran/methanol mixture. 112 mg of sodium hydroxide (2.79 mmol, 4 eq.) dissolved in 6 mL of water are added and stirring is continued for 18 hours. The reaction medium is evaporated. The residue is taken up in water and washed twice with diethyl ether. The aqueous phase is partially concentrated and acidified with an aqueous 6% sulfur dioxide solution. The aqueous phase is partially concentrated, drained and washed successively with water and with diethyl ether. 0.19 mg of cis-4-[4-(5-cyclopentylamino[1.3.4]thiadiazol-2-ylcarbamoyl)phenoxy]cyclohexanecarboxylic acid is obtained.

Workup

  1. additionare added
  2. customThe reaction medium is evaporated
  3. washwashed twice with diethyl ether
  4. concentrationThe aqueous phase is partially concentrated
  5. concentrationThe aqueous phase is partially concentrated
  6. washwashed successively with water and with diethyl ether

Sources & evidence

ORD record
ord-36250ee98bb9401a82da64e1eeeeacd2
Source dataset
uspto-grants-2013_10
Patent number
US08546391B2

Reaction notes

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