1,1'-(Diazomethylene)bis(benzene) → HCID 54207516, compound

HRID 1446945Notes

Reaction equation

HRID 1446945 reaction equation
[C:1]1([C:7]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[N+]=[N-])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:16]([NH:23][C@@H:24]([C:27]([OH:29])=[O:28])[CH2:25][OH:26])([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17]>C(Cl)Cl>[C:1]1([CH:7]([O:29][C:27](=[O:28])[C@@H:24]([CH2:25][OH:26])[NH:23][C:16]([O:18][C:19]([CH3:20])([CH3:22])[CH3:21])=[O:17])[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 612301,1'-(Diazomethylene)bis(benzene)HCID 637603(R)-2-tert-butoxycarbonylamino-3-hydroxy propionic acid

Product 1

HCID 54207516HCID 54207516, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of approximately 214 g of diphenyldiazomethane in 1 l of methylene chloride is added dropwise at 22°, while cooling, to a solution of 236.7 g of the resulting crude (2R)-BOC-serine in 700 ml of methylene chloride and the mixture is stirred for 11/2 hours at 20°. The mixture is concentrated by evaporation in vacuo, the residue is taken up in ethyl acetate and washed at 0° with a phosphate buffer of a pH of 2.0 then of a pH of 7.0. The dried organic phase yields a crystalline residue on concentration by evaporation which is digested in hexane and, after filtering, (2R)-N-BOC-serine diphenylmethyl ester is obtained; m.p. 116°-117° (corrected).

Workup

  1. concentrationThe mixture is concentrated by evaporation in vacuo
  2. washwashed at 0° with a phosphate buffer of a pH of 2.0
  3. customThe dried organic phase yields a crystalline residue
  4. concentrationon concentration
  5. customby evaporation which
  6. filtrationafter filtering

Sources & evidence

ORD record
ord-04d255a9f8474ba499b7f160676d3cfa
Source dataset
uspto-grants-1982_02
Patent number
US04313945

Reaction notes

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