Triethylamine → (S)-4-(Benzyloxycarbonyl)-1-(diphenylcarbamoyl)piperazine-2-carboxylic acid

HRID 486746Notes

Reaction equation

HRID 486746 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][NH:14][C@H:13]([C:17]([OH:19])=[O:18])[CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.[C:27]1([N:33]([C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)[C:34](Cl)=[O:35])[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>CN(C=O)C>[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][N:14]([C:34](=[O:35])[N:33]([C:37]2[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=2)[C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[C@H:13]([C:17]([OH:19])=[O:18])[CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 65741N,N-Diphenylcarbamic chlorideHCID 1514273(S)-4-(Benzyloxycarbonyl)piperazine-2-carboxylic acid

Product 1

HCID 54084760(S)-4-(Benzyloxycarbonyl)-1-(diphenylcarbamoyl)piperazine-2-carboxylic acid

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 1.03 g (3.90 mmole) of (S)-4-(benzyloxycarbonyl)piperazine-2-carboxylic acid (from Step A) in 12 ml. of DMF was treated with 0.788 g (7.79 mmole) of triethylamine at 25° C. With stirring 0.901 g (3.89 mmole) of diphenylcarbamoyl chloride was added in portions over 2 hours. After 16 hours the mixture was concentrated in vacuo to an orange oil which was chromatographed over an 88×2.5 cm LH 20 column with 11 ml. fractions of methanol. Fractions 35-43 were combined and concentrated to 1.136 g (64%) of pale yellow oil which contained a major spot by TLC (80:18:2 chloroform methanol ammonia water, Rf =0.45).

Workup

  1. additionwas added in portions over 2 hours
  2. concentrationAfter 16 hours the mixture was concentrated in vacuo to an orange oil which
  3. customwas chromatographed over an 88×2.5 cm LH 20 column with 11 ml
  4. concentrationconcentrated to 1.136 g (64%) of pale yellow oil which

Sources & evidence

ORD record
ord-a90cd6b39b3c498d8daeb6a23ddf4976
Source dataset
uspto-grants-1994_03
Patent number
US05292726

Reaction notes

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