Dichloromethane → Biphenyl-2-ylcarbamic Acid

HRID 1393820Notes

Reaction equation

HRID 1393820 reaction equation
[C:1]([OH:4])(=[O:3])C.NC[C@@H]([C:16]1[CH:25]=[CH:24][C:23](O)=[C:22]2[C:17]=1[CH:18]=[CH:19][C:20](=O)[NH:21]2)O[Si](C(C)(C)C)(C)C.C(O[BH-](O[C:38](=O)[CH3:39])OC(=O)C)(=O)C.[Na+].Cl[CH2:43]Cl>CO>[C:17]1([C:18]2[CH:19]=[CH:20][CH:39]=[CH:38][CH:43]=2)[CH:16]=[CH:25][CH:24]=[CH:23][C:22]=1[NH:21][C:1](=[O:3])[OH:4]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 5049666Sodium triacetoxyborohydrideHCID 666722995-[(R)-2-amino-1-(tert-butyldimethylsilanyloxy)ethyl]-8-hydroxy-1H-quinolin-2-one acetate

Product 1

HCID 607059Biphenyl-2-ylcarbamic Acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To the product from Preparation 97 in a mixture of dichloromethane (0.5 mL) and methanol (0.5 mL) was added 5-[(R)-2-amino-1-(tert-butyldimethylsilanyloxy)ethyl]-8-hydroxy-1H-quinolin-2-one acetate (124.1 mg, 3.1 mmol) and the resulting mixture was stirred at room temperature for 1.5 h. Sodium triacetoxyborohydride (190.7 mg, 0.9 mmol) was added and the resulting mixture was stirred at room temperature for 15 h. The reaction was quenched by adding water (about 0.2 mL) and the mixture was concentrated in vacuo to give the title compound, which was used without further purification. MS m/z 854.5 (M+H, expected 853.36 for C46H56ClN5O7Si).

Workup

  1. customTo the product from Preparation 97
  2. stirringthe resulting mixture was stirred at room temperature for 15 h
  3. customThe reaction was quenched
  4. additionby adding water (about 0.2 mL)
  5. concentrationthe mixture was concentrated in vacuo

Sources & evidence

ORD record
ord-24c1b8e0e7704bc5aa4a38ea6bca07f6
Source dataset
uspto-grants-2008_03
Patent number
US07345175B2

Reaction notes

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