Dicyclohexylcarbodiimide → HCID 13984254, compound

HRID 1607028Notes

Reaction equation

HRID 1607028 reaction equation
C1(N=C=NC2CCCCC2)CCCCC1.[C:16]([O:20][C:21](=[O:32])[CH2:22][NH:23][C:24]1[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[CH:26][CH:25]=1)([CH3:19])([CH3:18])[CH3:17].CC1(C)C2CCC1(C)[C:36](/[C:38]/2=[C:39](/[C:41](F)(F)F)\[OH:40])=[O:37].CC1(C)C2CCC1(C)[C:53](/C/2=C(/C(F)(F)F)\O)=[O:54].CC1(C)C2CCC1(C)C(/C/2=C(/C(F)(F)F)\O)=[O:71].[Eu]>C1COCC1>[C:16]([O:20][C:21]([CH2:22][N:23]([C:24]1[CH:25]=[CH:26][C:27]([O:30][CH3:31])=[CH:28][CH:29]=1)[C:36](=[O:37])[C@@H:38]1[O:40][C@@H:39]1[C:41]([O:54][CH3:53])=[O:71])=[O:32])([CH3:19])([CH3:18])[CH3:17]

Participants

5

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 6104361HCID 6104361, compoundHCID 11009985HCID 11009985, compound

Product 1

HCID 13984254HCID 13984254, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 188.0 g (0.88 mol) of dicyclohexylcarbodiimide in 300 ml of THF was added dropwise, within 15 minutes, to a solution of 129.0 g (0.88 mol) of monomethyl (2R,2S)-2,3-oxirandicarboxylate and 196.0 g (0.8 mol) of t-butyl-N-(4-methoxyphenyl)glycinate [M. Shiozaki et al., Tetrahedron 40, 1795, (1984)] in 1100 ml of THF. The mixture was subsequently stirred for a further 30 minutes at room temperature, the resultant precipitate was separated off by filtration, and the filtrate solution was evaporated in vacuo. After purification of the product on 1.8 kg of silica gel (toluene:ethyl acetate=7:3), 263.2 g (90% of theory) of the title compound were obtained as crystals, melting point: 89° C. [α]D20 =-21.78° (c=0.435 in CHCl3). The enantiomer ratio, of 3:2, determined in the preparation example was confirmed by NMR-shift experiments using Eu(TFC)3.

Workup

  1. customthe resultant precipitate was separated off by filtration
  2. customthe filtrate solution was evaporated in vacuo
  3. customAfter purification of the product on 1.8 kg of silica gel (toluene:ethyl acetate=7:3), 263.2 g (90% of theory) of the title compound
  4. customwere obtained as crystals, melting point: 89° C. [α]D20 =-21.78° (c=0.435 in CHCl3)

Sources & evidence

ORD record
ord-3132852e26eb462881296ea1cfe28d55
Source dataset
uspto-grants-1989_09
Patent number
US04863916

Reaction notes

Loading…