Acetic Acid → HCID 57299430, compound

HRID 5616Notes

Reaction equation

HRID 5616 reaction equation
Cl.[C:2]1(NCC(OC)=O)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:14][C:15]([OH:17])=[O:16].[C:18]1([CH2:24][N:25]2[C:33]3[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=3)[C:27](C=O)=[CH:26]2)[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.[BH3-][C:37]#[N:38].[Na+].[CH3:40]O>>[C:18]1([CH2:24][N:25]2[C:33]3[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=3)[C:27]([CH2:37][NH:38][CH:14]([C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)[C:15]([O:17][CH3:40])=[O:16])=[CH:26]2)[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

Participants

6

Reactant 5

HCID 176Acetic AcidHCID 887MethanolHCID 2621041-benzyl-1H-indole-3-carbaldehydeHCID 5003444Sodium cyanoborohydrideHCID 12241365Methyl 2-(phenylamino)acetate hydrochloride

Product 1

HCID 57299430HCID 57299430, compoundYield 43%

Procedure

To a suspension of methyl (+/-)-phenylglycinate hydrochloride (4.00 g, 19.8 mmol) in MeOH (50 mL), and HOAc (4 mL) was added 1-phenylmethyl-indole-3-carboxaldehyde (2.85 g, 12.1 mmol). The resulting mixture was allowed to stir at room temperature for 20 minutes; then NaBH3CN (1.98 g, 31.5 mmol) was added in one portion. The suspension was allowed to stir at room temperature for 18 hours, then was concentrated in vacuo to furnish a sticky white semi-solid. The crude reaction mixture was partitioned between 20% aqueous NaOH (0.25 L) and EtOAc (0.25 L); the organic phase was separated, washed with brine (0.25 L), and dried (Na2SO4). Concentration in vacuo afforded the crude product as a pale green oil which was purified by chromatography on a column of silica gel (230-400 mesh, 500 g, 70 mm o.d., EtOAc-hexanes 25:75, 400 mL fractions) using the flash technique. Fractions 8-13 were combined to provide 2.0 g (43%) of the title compound as a white solid. Recrystallization from EtOAc-hexanes provided white needles, m.p. 109°-110° C.

Workup

  1. stirringto stir at room temperature for 18 hours
  2. concentrationwas concentrated in vacuo
  3. customto furnish a sticky white semi-solid
  4. customThe crude reaction mixture
  5. customwas partitioned between 20% aqueous NaOH (0.25 L) and EtOAc (0.25 L)
  6. customthe organic phase was separated
  7. washwashed with brine (0.25 L)
  8. dry with materialdried (Na2SO4)
  9. concentrationConcentration in vacuo
  10. customafforded the crude product as a pale green oil which
  11. customwas purified by chromatography on a column of silica gel (230-400 mesh, 500 g, 70 mm o.d., EtOAc-hexanes 25:75, 400 mL fractions)

Sources & evidence

ORD record
ord-c456b7da73ac4e6ca23b379fc52bb58b
Source dataset
uspto-grants-1993_09
Patent number
US05245046

Reaction notes

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