Triethylamine → BOC-MeLeu-Ala-Bzl

HRID 1583839Notes

Reaction equation

HRID 1583839 reaction equation
C(Cl)(=O)C(C)(C)C.C(N(CC)CC)C.[C:15]([N:22]([CH3:31])[C@H:23]([C:28]([OH:30])=O)[CH2:24][CH:25]([CH3:27])[CH3:26])([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16].[NH2:32][C@H:33]([C:35]([CH2:37][C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)=[O:36])[CH3:34]>C(Cl)(Cl)Cl>[C:15]([N:22]([CH3:31])[C@H:23]([C:28]([NH:32][C@H:33]([C:35]([CH2:37][C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)=[O:36])[CH3:34])=[O:30])[CH2:24][CH:25]([CH3:26])[CH3:27])([O:17][C:18]([CH3:19])([CH3:20])[CH3:21])=[O:16]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 62493Pivaloyl chlorideHCID 7010555(2S)-2-{[(tert-butoxy)carbonyl](methyl)amino}-4-methylpentanoic acidHCID 70301976H-Ala-Bzl

Product 1

HCID 131713049BOC-MeLeu-Ala-Bzl

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

23.3 ml (18.9 g=157 mMol) pivaloyl chloride and 48 ml (28.9 g=286 mMol) triethylamine are added to a solution of 35 g (143 mMol) BOC-MeLeu-OH in 500 ml chloroform and the mixture stirred for 2 hrs. at room temperature under a nitrogen atmosphere. 30.7 g (171 mMol) H-Ala-Bzl dissolved in 300 ml chloroform are then added and the reaction mixture stirred for a further 2 hrs. at room temperature, again under a nitrogen atmosphere. The product is purified in accordance with the technique of example 1a) to yield the title compound: rotation, [α]D25 =-59.4° (c=1.0 in chloroform).

Workup

  1. customat room temperature
  2. additionare then added
  3. stirringthe reaction mixture stirred for a further 2 hrs
  4. customat room temperature
  5. customThe product is purified in accordance with the technique of example 1a)

Sources & evidence

ORD record
ord-89ae089a8a3f42c494bb7f7c0bd26ff4
Source dataset
uspto-grants-1985_11
Patent number
US04554351

Reaction notes

Loading…