1,2-Dichloroethane → HCID 59753406, compound

HRID 751749Notes

Reaction equation

HRID 751749 reaction equation
[C:1]([N:8]1[CH2:15][CH2:14][CH2:13][C@H:9]1[C:10]([OH:12])=[O:11])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[CH2:16]([O:23][C:24]([NH:26][C@@H:27]([CH2:40]O)[C:28]([O:30][CH2:31][C:32](=[O:39])[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)=[O:29])=[O:25])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.C(Cl)CCl.C1(C)C=CC=CC=1.C(OCC)(=O)C>C(Cl)Cl.CN(C1C=CN=CC=1)C>[N:8]1([C:1]([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2])[CH2:15][CH2:14][CH2:13][C@H:9]1[C:10]([O:12][CH2:40][C@H:27]([NH:26][C:24]([O:23][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:25])[C:28]([O:30][CH2:31][C:32](=[O:39])[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)=[O:29])=[O:11]

Participants

7

Reactant 4

HCID 111,2-DichloroethaneHCID 850831,2-Pyrrolidinedicarboxylic acid, 1-(1,1-dimethylethyl) ester, (2S)-HCID 11078819HCID 11078819, compoundHCID 21584019Toluene ethylacetate

Product 1

HCID 59753406HCID 59753406, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
-20 °C

Procedure

15.06 g of N-Boc-(L)-proline (69.96 mmol) and 25.00 g (69.96 mmol) of the serine ester from example 1A are dissolved in methylene chloride (250 ml) under argon. The solution is cooled to −20° C. and treated with 13.41 g of EDC (69.96 mmol) and 0.85 g of DMAP (7.00 mmol). The reaction solution is stirred at −20° C. for 1 h and then at room temperature for 48 h, evaporated and the residue is taken up in ethyl acetate. The solution is washed with aq. citric acid, aq. saturated sodium hydrogen-carbonate solution and aq. saturated sodium chloride solution. The organic phase is dried over sodium sulfate and evaporated. 32.47 g (84% of th.) of product are isolated after silica gel chromatography using toluene/ethyl acetate (5/1).

Workup

  1. waitat room temperature for 48 h
  2. customevaporated
  3. washThe solution is washed with aq. citric acid, aq. saturated sodium hydrogen-carbonate solution and aq. saturated sodium chloride solution
  4. dry with materialThe organic phase is dried over sodium sulfate
  5. customevaporated
  6. custom32.47 g (84% of th.) of product are isolated after silica gel chromatography

Sources & evidence

ORD record
ord-c18abbc71ec342b28866971797f7f635
Source dataset
uspto-grants-2008_07
Patent number
US07405201B2

Reaction notes

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