1,2-Dichloroethane → HCID 131719117, compound

HRID 2399237Notes

Reaction equation

HRID 2399237 reaction equation
C(Cl)CCl.[N:5]1([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:12][CH2:11][CH2:10][C@@H:6]1[C:7]([OH:9])=O.OC1C2N=NNC=2C=CC=1.C(N(CC)CC)C.FC(F)(F)C([O-])=O.[NH2:44][C@@H:45]([C:53]([O:55][CH2:56][C:57]1[CH:62]=[CH:61][CH:60]=[CH:59][CH:58]=1)=[O:54])[CH2:46][C:47]1[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=1>ClCCl>[N:5]1([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:12][CH2:11][CH2:10][C@@H:6]1[C:7]([NH:44][C@@H:45]([C:53]([O:55][CH2:56][C:57]1[CH:62]=[CH:61][CH:60]=[CH:59][CH:58]=1)=[O:54])[CH2:46][C:47]1[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=1)=[O:9]

Participants

8

Reactant 6

HCID 111,2-DichloroethaneHCID 8471TriethylamineHCID 84468TrifluoroacetateHCID 688022(2R)-1-[(tert-butoxy)carbonyl]pyrrolidine-2-carboxylic acidHCID 853473HCID 853473, compoundHCID 178418300HCID 178418300, compound

Product 1

HCID 131719117HCID 131719117, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

EDC (1.68 g, 8.78 mmol) was added to a solution of N-Boc-D-Pro (372 mg, 1.73 mmol) and hydroxybenzotriazole (281 mg, 2.08 mmol) in dry dichloromethane (17.3 ml) and the resulting mixture was stirred at room temperature for 2.5 hours. Distilled triethylamine (482 μl, 3.46 mmol) was then added, followed by the crude trifluoroacetate salt of D-Phe-OBn, prepared as described above. The solution was stirred for an additional 3 hours, diluted with dichloromethane and washed sequentially with a dilute solution of HCl (<5%, pH 3.0), a solution of saturated sodium bicarbonate, and brine. The combined organic layers were dried over MgSO4 and concentrated to obtain a yellow oil. This substance was subjected to silica gel chromatography, eluted with a solution that was 2:1 hexanes:ethyl acetate, and resulted in a yield of 658 mg of N-Boc-D-Pro-D-Phe-OBn as a clear oil.

Workup

  1. customprepared
  2. stirringThe solution was stirred for an additional 3 hours
  3. washwashed sequentially with a dilute solution of HCl (<5%, pH 3.0)
  4. dry with materialThe combined organic layers were dried over MgSO4
  5. concentrationconcentrated
  6. customto obtain a yellow oil
  7. washeluted with a solution that

Sources & evidence

ORD record
ord-f47733bea197410c9af041fecda2eef6
Source dataset
uspto-grants-1995_09
Patent number
US05447915

Reaction notes

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