Sodium Bicarbonate → HCID 71711171, compound

HRID 2403200Notes

Reaction equation

HRID 2403200 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8]([C@H:11]1[CH2:15][N:14]([C:16]([C:18]2([N:21]3[CH2:26][CH2:25][N:24](C(OC(C)(C)C)=O)[CH2:23][CH2:22]3)[CH2:20][CH2:19]2)=[O:17])[C@H:13]([C:34](=[O:41])[NH:35][C:36]2([C:39]#[N:40])[CH2:38][CH2:37]2)[CH2:12]1)(=[O:10])=[O:9].C(=O)([O-])O.[Na+]>C(O)=O.O>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8]([C@H:11]1[CH2:15][N:14]([C:16]([C:18]2([N:21]3[CH2:22][CH2:23][NH:24][CH2:25][CH2:26]3)[CH2:19][CH2:20]2)=[O:17])[C@H:13]([C:34]([NH:35][C:36]2([C:39]#[N:40])[CH2:37][CH2:38]2)=[O:41])[CH2:12]1)(=[O:10])=[O:9]

Participants

5

Reactant 2

HCID 516892Sodium Bicarbonate2×HCID 71711170HCID 71711170, compound

Product 1

HCID 71711171HCID 71711171, compoundYield 73.2%

Reagents, catalysts & solvents 2

HCID 284Formic AcidSolventHCID 962WaterSolvent

Procedure

A solution of tert-butyl 4-(1-((2S,4R)-4-(2-chlorophenylsulfonyl)-2-(1-cyanocyclopropylcarbamoyl)pyrrolidine-1-carbonyl)cyclopropyl)piperazine-1-carboxylate (367 mg, 605 μmol) in formic acid (6.05 mL) was stirred at room temperature for 5 hours. The reaction was diluted with water under ice cooling and set to pH 7-8 slowly by first adding saturated aqueous sodium hydrogen carbonate solution and then with solid sodium hydrogen carbonate. The reaction was extracted three times with methylenechloride. The combined organic layers were washed with saturated aqueous sodium chloride solution, dried over sodium sulfate, filtered and the solvent was evaporated under reduced pressure to yield the title compound as a light yellow foam (224 mg, 73%). MS ISP (m/e): 506.1/508.2 (100/45) [(M+H)]+.

Workup

  1. extractionThe reaction was extracted three times with methylenechloride
  2. washThe combined organic layers were washed with saturated aqueous sodium chloride solution
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-c86eea3796ba42518960814101a3f31e
Source dataset
uspto-grants-2014_08
Patent number
US08802665B2

Reaction notes

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