Triethylamine → HCID 131713673, compound

HRID 2417866Notes

Reaction equation

HRID 2417866 reaction equation
Br[CH2:2][C:3]([O:5][C:6]([CH3:9])([CH3:8])[CH3:7])=[O:4].C(N(CC)CC)C.ClC(OCC1C=CC=CC=1)=O.CC(C(OC(=O)C[N:37]([C:57]([O:59][CH2:60][C:61]1[CH:66]=[CH:65][CH:64]=[CH:63][CH:62]=1)=[O:58])[C@H:38]([C:40]([N:42]1[CH2:56][CH2:55][CH2:54][C@H:43]1[C:44]([O:46][CH2:47][C:48]1[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=1)=[O:45])=[O:41])[CH3:39])C)(C)C>O1CCCC1>[CH3:7][C:6]([CH3:9])([O:5][C:3](=[O:4])[CH2:2][N:37]([C:57]([O:59][CH2:60][C:61]1[CH:66]=[CH:65][CH:64]=[CH:63][CH:62]=1)=[O:58])[C@H:38]([C:40]([N:42]1[CH2:56][CH2:55][CH2:54][C@H:43]1[C:44]([O:46][CH2:47][C:48]1[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=1)=[O:45])=[O:41])[CH3:39])[CH3:8]

Participants

6

Reactant 4

HCID 8471Triethylamine2×HCID 10387Benzyl chloroformateHCID 79177tert-Butyl bromoacetateHCID 131713674HCID 131713674, compound

Product 1

HCID 131713673HCID 131713673, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of L-alanyl-L-proline, phenylmethyl ester, p-toluenesulfonic acid salt (32.16 g., 72 mmole), tert-butyl bromoacetate (14.2 g., 72 mmole), triethylamine (20.1 ml., 144 mmole), and tetrahydrofuran (290 ml.) are stirred at room temperature for 72 hours. Benzyl chloroformate (12.4 ml., 87.8 mmole) and triethylamine (12.5 ml., 87.8 mmole) are added and the mixture stirred overnight. The reaction product is evaporated, and partitioned between water and ethyl acetate. The ethyl acetate solubles are washed with dilute hydrochloric acid and then water. The ethyl acetate solution is then evaporated and chromatographed over silica gel (mesh 230-400) using the solvent system ethyl acetate/hexane (1:1) (10 psi pressure) to give 19.5 g. of 1-[N-[2-(1,1-dimethylethylethoxy)-2-oxoethyl]-N-[(phenylmethoxy)carbonyl]-L-alanyl]-L-proline, phenylmethyl ester.

Workup

  1. stirringthe mixture stirred overnight
  2. customThe reaction product is evaporated
  3. custompartitioned between water and ethyl acetate
  4. washThe ethyl acetate solubles are washed with dilute hydrochloric acid
  5. customThe ethyl acetate solution is then evaporated
  6. customchromatographed over silica gel (mesh 230-400)
  7. customto give 19.5 g

Sources & evidence

ORD record
ord-3bbf348bf8444262ac5d46acf03e5147
Source dataset
uspto-grants-1984_09
Patent number
US04470973

Reaction notes

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