Benzylamine → HCID 2363706, compound

HRID 441892Notes

Reaction equation

HRID 441892 reaction equation
[CH2:1]([NH2:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Na].SC1C=CC=CN=1.ClC1C([O:24][C:25](=O)[C@H:26]([CH:38]([CH3:40])[CH3:39])[NH:27][C:28]([O:30][CH2:31][C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)=[O:29])=C(Cl)C(Cl)=C(Cl)C=1Cl>ClCCl>[CH2:1]([NH:8][C:25](=[O:24])[C@H:26]([CH:38]([CH3:39])[CH3:40])[NH:27][C:28]([O:30][CH2:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)=[O:29])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 7504BenzylamineHCID 5360545SodiumHCID 22790965HCID 22790965, compoundHCID 178418616HCID 178418616, compound

Product 1

HCID 2363706HCID 2363706, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1.1 ml. of benzylamine is dissolved in 200 ml. of dichloromethane, and 0.13 g. of the sodium salt of 2-mercaptopyridine is suspended therein. Then, 5.0 g. of benzyloxy carbonyl-L-valine pentachlorophenyl ester is added thereto. As determined by thin layer chromatography, the period required to consume one-half of the reactants is about 10 minutes. After three hours, treatment is effected in the same manner as in the previous example, and the dichloromethane layer is concentrated, whereby 3.1 g. of crude crystals are obtained (yield: 91 percent). By recrystallization from ethyl acetate, 2.7 g. of needle-like crystals are obtained. m.p. 174.5° C.

Workup

  1. customto consume one-half of the reactants
  2. waitAfter three hours
  3. concentrationthe dichloromethane layer is concentrated
  4. customof crude crystals are obtained (yield: 91 percent)
  5. customBy recrystallization from ethyl acetate, 2.7 g
  6. customof needle-like crystals are obtained

Sources & evidence

ORD record
ord-01f620fb09e24fc99c9ad6aa8e490a70
Source dataset
uspto-grants-1977_08
Patent number
USRE029369

Reaction notes

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