Citric Acid → HCID 67507507, compound

HRID 1829114Notes

Reaction equation

HRID 1829114 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][C@@H:11]([NH:13][S:14]([C:17]2[CH:22]=[CH:21][C:20]([C:23]#[N:24])=[CH:19][CH:18]=2)(=[O:16])=[O:15])[CH2:10][C@H:9]1[C:25]([N:27]1[CH2:31][CH2:30][S:29][CH2:28]1)=[O:26])=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl.C(C1C=CC(S(N[C@@H]2CN[C@H](C(N3CCSC3)=O)C2)(=O)=O)=CC=1)#N.C(=O)([O-])[O-].[K+].[K+].[C:63]([C:65]1[CH:72]=[CH:71][C:68]([CH2:69]Br)=[CH:67][CH:66]=1)#[N:64].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>CN(C=O)C>[C:1]([O:5][C:6]([N:8]1[CH2:12][C@@H:11]([N:13]([CH2:69][C:68]2[CH:71]=[CH:72][C:65]([C:63]#[N:64])=[CH:66][CH:67]=2)[S:14]([C:17]2[CH:18]=[CH:19][C:20]([C:23]#[N:24])=[CH:21][CH:22]=2)(=[O:15])=[O:16])[CH2:10][C@H:9]1[C:25]([N:27]1[CH2:31][CH2:30][S:29][CH2:28]1)=[O:26])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

7

Reactant 5

HCID 311Citric AcidHCID 11430Potassium CarbonateHCID 869964-(Bromomethyl)benzonitrileHCID 67507232HCID 67507232, compoundHCID 67507766HCID 67507766, compound

Product 1

HCID 67507507HCID 67507507, compoundYield 84.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3-[(2S,4S)-1-tert-Butoxycarbonyl-4-(4-cyanophenylsulfonyl)amino-2-pyrrolidinylcarbonyl]-1,3-thiazolidine [product of Example 123 (1), 856 mg] was dissolved in DMF (20 mL), and potassium carbonate (380 mg) and 4-cyanobenzyl bromide (400 mg) were added thereto at room temperature. The mixture was stirred for 4 hr. To the reaction mixture was added 10% citric acid solution, and the precipitate was collected by filtration to give 3-{(2S,4S)-1-tert-butoxycarbonyl-4-[N-(4-cyanophenylmethyl)-N-(4-cyanophenylsulfonyl)amino]-2-pyrrolidinylcarbonyl}-1,3-thiazolidine (900 mg) as a pale-yellow solid.

Workup

  1. customat room temperature
  2. filtrationthe precipitate was collected by filtration

Sources & evidence

ORD record
ord-31b6c6ea8beb457688310cef44ec0d5f
Source dataset
uspto-grants-2006_06
Patent number
US07060722B2

Reaction notes

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