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N-(Diphenylmethylene)glycine tert-butyl ester → 2-(Benzhydrylidene-amino)-3-cycloheptyl-propionic acid tert-butyl ester

HRID 1018846
Notes
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Reaction equation

HRID 1018846 reaction equation
[C:1]([O:5][C:6](=[O:22])[CH2:7][N:8]=[C:9]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)([CH3:4])([CH3:3])[CH3:2].C([N-]C(C)C)(C)C.[Li+].[CH:31]1([CH2:38]I)[CH2:37][CH2:36][CH2:35][CH2:34][CH2:33][CH2:32]1>O1CCCC1>[C:1]([O:5][C:6](=[O:22])[CH:7]([N:8]=[C:9]([C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1)[C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1)[CH2:38][CH:31]1[CH2:37][CH2:36][CH2:35][CH2:34][CH2:33][CH2:32]1)([CH3:4])([CH3:2])[CH3:3]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 688171N-(Diphenylmethylene)glycine tert-butyl esterHCID 2724682Lithium diisopropylamideHCID 2763013Iodomethylcycloheptane

Product 1

HCID 865853992-(Benzhydrylidene-amino)-3-cycloheptyl-propionic acid tert-butyl esterYield 73%

Reagents, catalysts & solvents 1

HCID 8028Tetrahydrofuran
Solvent
2×

Procedure

To a stirred solution of (Benzhydrylidene-amino)-acetic acid tert-butyl ester (2.56 g; 8.68 mmol) in 30 mL of tetrahydrofuran under argon at −78° C. was added lithium diisopropylamide solution (10.0 mL; 1.5 M solution in cyclohexane) dropwise. After 30 minutes, a solution of cycloheptylmethyl iodide (Prepared in Step B; 3.48 g; 14.6 mmol) in 20 mL tetrahydrofuran was added dropwise and the mixture allowed to warm to room temperature and stirred for 18 h. The mixture was quenched with saturated ammonium chloride solution (100 mL). The layers were separated and the aqueous layer was extracted with ethyl acetate. The combined organic layers were dried (sodium sulfate) filtered and concentrated in vacuo. The crude product was chromatographed (Biotage 40M; eluent: 5% ethyl acetate/hexanes) to give 2.56 g (73%) of 2-(Benzhydrylidene-amino)-3-cycloheptyl-propionic acid tert-butyl ester as a pale yellow oil.

Workup

  1. customThe mixture was quenched with saturated ammonium chloride solution (100 mL)
  2. customThe layers were separated
  3. extractionthe aqueous layer was extracted with ethyl acetate
  4. dry with materialThe combined organic layers were dried (sodium sulfate)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe crude product was chromatographed (Biotage 40M; eluent: 5% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-1acd85e0fa9e4ad897b3a0cf47553bc7
Source dataset
uspto-grants-2002_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06482951B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes