N-(tert-butoxycarbonyl)glycine → HCID 22458407, compound

HRID 2185447Notes

Reaction equation

HRID 2185447 reaction equation
O=C1N(P(Cl)(N2CCOC2=O)=O)CCO1.C(N(CC)C(C)C)(C)C.[CH:25]1[CH:30]=[CH:29][C:28]([CH2:31][C:32]2[CH:37]=[CH:36][C:35]([NH2:38])=[CH:34][CH:33]=2)=[CH:27][CH:26]=1.[C:39]([O:43][C:44]([NH:46][CH2:47][C:48](O)=[O:49])=[O:45])([CH3:42])([CH3:41])[CH3:40]>ClCCl>[CH2:31]([C:32]1[CH:33]=[CH:34][C:35]([NH:38][C:48](=[O:49])[CH2:47][NH:46][C:44]([O:43][C:39]([CH3:41])([CH3:40])[CH3:42])=[O:45])=[CH:36][CH:37]=1)[C:28]1[CH:27]=[CH:26][CH:25]=[CH:30][CH:29]=1

Participants

6

Reactant 4

HCID 78288N-(tert-butoxycarbonyl)glycineHCID 81531DiisopropylethylamineHCID 136914Benzenamine, 4-(phenylmethyl)-HCID 152842Bis(2-oxo-3-oxazolidinyl)phosphinic chloride

Product 1

HCID 22458407HCID 22458407, compoundYield 83.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Bis(2-oxo-3-oxazolidinyl)phosphinic chloride (1.90 g) and N,N-diisopropylethyl-amine (1.5 mL) were added to a solution of 4-aminodiphenylmethane (0.52 g) and N-tert-butoxycarbonylglycine (0.50 g) in dichloromethane (30 mL) at 0° C. After stiriing at 0° C. for 10 min and at room temperature for 17.5 hr, the solvent was removed in vacuo. The residue was diluted with 1 N hydrochloric acid and extracted with ethyl acetate. The organic layer was washed with water, saturated sodium hydrogen carbonate, and brine, dried over anhydrous sodium sulfate, and evaporated in vacuo. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=3:1, v/v) to afford the title compound (0.81 g) as a colorless powder: 1H NMR (400 MHz, CDCl3) δ 1.47 (s, 9H), 3.90 (d, 2H), 3.94 (s, 2H), 7.12-7.21 (m, 5H), 7.28 (d, 2H), 7.41 (d, 2H).

Workup

  1. customthe solvent was removed in vacuo
  2. additionThe residue was diluted with 1 N hydrochloric acid
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with water, saturated sodium hydrogen carbonate, and brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. customevaporated in vacuo
  7. customThe residue was purified by silica gel column chromatography (hexane

Sources & evidence

ORD record
ord-21b9ad97c6d748caaeb9f330a3714a72
Source dataset
uspto-grants-2002_06
Patent number
US06399629B1

Reaction notes

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