Benzylamine → HCID 2363706, compound

HRID 1658405Notes

Reaction equation

HRID 1658405 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 benzyloxycarbonyl-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 3 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%). 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 3 hours
  3. concentrationthe dichloromethane layer is concentrated
  4. customof crude crystals are obtained (yield: 91%)
  5. customBy recrystallization from ethyl acetate, 2.7 g
  6. customof needle-like crystals are obtained

Sources & evidence

ORD record
ord-10b5c9d733114138b26dcad4d027a2c4
Source dataset
uspto-grants-1976_06
Patent number
US03963728

Reaction notes

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