Citric Acid → HCID 68677751, compound

HRID 1158517Notes

Reaction equation

HRID 1158517 reaction equation
[NH2:1][C@@H:2]1[C:9]2[CH:8]=[CH:7][S:6][C:5]=2[CH2:4][C@@H:3]1[OH:10].[C:11]([NH:18][C@H:19]([C:27](O)=[O:28])[CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12].CCN=C=NCCCN(C)C.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>CN(C=O)C>[C:14]([O:13][C:11](=[O:12])[NH:18][CH:19]([C:27](=[O:28])[NH:1][CH:2]1[C:9]2[CH:8]=[CH:7][S:6][C:5]=2[CH2:4][CH:3]1[OH:10])[CH2:20][C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1)([CH3:15])([CH3:17])[CH3:16]

Participants

6

Reactant 4

HCID 311Citric AcidHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 77857L-Phenylalanine, N-[(1,1-dimethylethoxy)carbonyl]-HCID 59511560HCID 59511560, compound

Product 1

HCID 68677751HCID 68677751, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of the racemic cis-4-amino-5,6-dihydro-4H-cyclopenta[b]thiophen-5-ol (17.5 g, 0.112 mol) in dry DMF (400 mL) was added Boc-L-phenylalanin (30.51 g, 0.115 mol) HOBT (15.6 g, 0.115 mol) and EDAC (22.0 g, 0.115 mol). To the stirred mixture was added TEA (16 mL, 0.115 mol) and the mixture was stirred at room temperature overnight. The mixture was added to 5% citric acid and extracted three times with ethyl acetate. The organic phase was washed with brine and saturated sodium hydrogen carbonate (two times). The organic phase was dried with sodium sulphate and evaporated under reduced pressure. Yield: 43 g=95%

Workup

  1. extractionextracted three times with ethyl acetate
  2. washThe organic phase was washed with brine and saturated sodium hydrogen carbonate (two times)
  3. dry with materialThe organic phase was dried with sodium sulphate
  4. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-767a4b185a114d74ae3d52aa09697312
Source dataset
uspto-grants-2010_10
Patent number
US07807677B2

Reaction notes

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