Glycine tert-butyl ester hydrochloride → HCID 68505688, compound

HRID 1714061Notes

Reaction equation

HRID 1714061 reaction equation
[CH:1]1([C:7]2[C:15]3[C:10](=[CH:11][C:12]([C:16]([O:18][CH3:19])=[O:17])=[CH:13][CH:14]=3)[N:9]([CH2:20][CH:21]([O:24][CH3:25])[O:22][CH3:23])[C:8]=2[C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=2[CH:32]=O)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.Cl.[NH2:35][CH2:36][C:37]([O:39][C:40]([CH3:43])([CH3:42])[CH3:41])=[O:38].[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>ClCCCl>[CH:1]1([C:7]2[C:15]3[C:10](=[CH:11][C:12]([C:16]([O:18][CH3:19])=[O:17])=[CH:13][CH:14]=3)[N:9]([CH2:20][CH:21]([O:22][CH3:23])[O:24][CH3:25])[C:8]=2[C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=2[CH2:32][NH:35][CH2:36][C:37]([O:39][C:40]([CH3:43])([CH3:42])[CH3:41])=[O:38])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

5

Reactant 3

HCID 2725036Glycine tert-butyl ester hydrochlorideHCID 5049666Sodium triacetoxyborohydrideHCID 86604965HCID 86604965, compound

Product 1

HCID 68505688HCID 68505688, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To a solution of methyl 3-cyclohexyl-1-(2,2-dimethoxyethyl)-2-(2-formylphenyl)-1H-indole-6-carboxylate (prepared as described in Example 20, Step 2) in DCE (0.09 M), tert-butyl glycinate hydrochloride salt (1.5 eq) was added followed by NaBH(OAc)3 (3 eq). The solution was stirred at RT for 2 days. The reaction was quenched with aqueous NaHCO3 and extracted with EtOAc (×2). The combined organic phases were washed with brine, dried (Na2SO4), filtered and concentrated in vacuo to give the title compound as a viscous oil (quantitative); MS (ES+) m/z 565 (M+H)+

Workup

  1. customThe reaction was quenched with aqueous NaHCO3
  2. extractionextracted with EtOAc (×2)
  3. washThe combined organic phases were washed with brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-3de4045243734f5a837acfd41a018c62
Source dataset
uspto-grants-2010_09
Patent number
US07795247B2

Reaction notes

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