L-Proline 1,1-dimethylethyl ester → N-[(Phenylmethoxy)carbonyl]-L-alanyl-L-proline 1,1-dimethylethyl ester

HRID 1580896Notes

Reaction equation

HRID 1580896 reaction equation
[CH3:1][C@H:2]([NH:15][C:16]([O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[O:17])[C:3]([O:5]C1C=CC([N+]([O-])=O)=CC=1)=O.[NH:26]1[CH2:37][CH2:36][CH2:35][C@H:27]1[C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29]>C(OCC)(=O)C>[NH:15]([C:16]([O:18][CH2:19][C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1)=[O:17])[C@H:2]([C:3]([N:26]1[CH2:37][CH2:36][CH2:35][C@H:27]1[C:28]([O:30][C:31]([CH3:33])([CH3:34])[CH3:32])=[O:29])=[O:5])[CH3:1]

Participants

4

Reactant 2

HCID 6453108L-Proline 1,1-dimethylethyl esterHCID 70218781168-87-2

Product 1

HCID 54380188N-[(Phenylmethoxy)carbonyl]-L-alanyl-L-proline 1,1-dimethylethyl ester

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

10.32 g of Z-Ala-ONP and 5.0 g of H-Pro-OtBu in 10 ml of ethyl acetate are allowed to stand for one hour at 0°C and 15 hours at room temperature. The mixture is then diluted with 100 ml of ethyl acetate, washed with 50 % saturated potassium carbonate solution and water, dried over sodium sulphate and evaporated. The resulting oil is homogeneous according to a thin layer chromatogram on silica gel (Rf = 0.65 in the system chloroform-methanol (9:1)) and is directly used further.

Workup

  1. washwashed with 50 % saturated potassium carbonate solution and water
  2. dry with materialdried over sodium sulphate
  3. customevaporated

Sources & evidence

ORD record
ord-d90b64e9800147c884a95fa370a57137
Source dataset
uspto-grants-1976_01
Patent number
US03934008

Reaction notes

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