Sodium Bicarbonate → HCID 57971739, compound

HRID 548264Notes

Reaction equation

HRID 548264 reaction equation
[C:1]([O:5][C:6](=[O:17])[NH:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([CH:15]=O)=[CH:11][CH:10]=1)([CH3:4])([CH3:3])[CH3:2].[CH:18]1([O:23][C:24](=[O:34])[C@H:25]([CH3:33])[NH:26]C2C=CC=CC=2)[CH2:22][CH2:21][CH2:20][CH2:19]1.C(O[BH-](O[C:45](=O)[CH3:46])OC(=O)C)(=O)C.[Na+].C(=O)(O)[O-].[Na+]>ClCCCl.C(Cl)Cl.C(O)(=O)C>[CH:18]1([O:23][C:24](=[O:34])[C@@H:25]([NH:26][CH2:15][C:12]2[CH:13]=[CH:14][C:9]([CH2:8][NH:7][C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:17])=[CH:10][CH:11]=2)[CH2:33][C:46]2[CH:45]=[CH:11][CH:10]=[CH:9][CH:8]=2)[CH2:19][CH2:20][CH2:21][CH2:22]1

Participants

8

Reactant 4

HCID 516892Sodium BicarbonateHCID 2794832tert-Butyl hydrogen ((4-formylphenyl)methyl)carbonimidateHCID 5049666Sodium triacetoxyborohydrideHCID 67052658HCID 67052658, compound

Product 1

HCID 57971739HCID 57971739, compound

Reagents, catalysts & solvents 3

HCID 111,2-DichloroethaneSolventHCID 176Acetic AcidSolventHCID 6344DichloromethaneSolvent

Procedure

(4-Formyl-benzyl)-carbamic acid tert-butyl ester (200 mg, 0.85 mmol) was dissolved in DCE (10 mL) and to this was added phenyl alanine cyclopentyl ester (214 mg, 0.94 mmol). The reaction was stirred at r.t. for 15 min. Sodium triacetoxyborohydride (538 mg, 2.55 mmol) and acetic acid (60 uL) were added and the reaction stirred for a further 1 h. Saturated sodium bicarbonate (10 ml) was added and the solution diluted with DCM (20 mL). The organic layer was isolated and concentrated to afford the desired product which was taken onto the next step without further purification. m/z 453 [M++H+

Workup

  1. stirringthe reaction stirred for a further 1 h
  2. customThe organic layer was isolated
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-9edc15f302f24a0b9413b2c071654305
Source dataset
uspto-grants-2011_05
Patent number
US07939666B2

Reaction notes

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