Formaldehyde → HCID 69129234, compound

HRID 1356212Notes

Reaction equation

HRID 1356212 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH2:9][C@H:10]([NH:24][S:25]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)(=[O:27])=[O:26])[C:11]([NH:13][CH2:14][CH2:15][CH2:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[O:12])[CH:5]=[CH:6][C:7]=1[OH:8].C=O.[BH-](OC(C)=O)(OC(C)=O)O[C:38](C)=O.[Na+].C([O-])(O)=O.[Na+]>ClC(Cl)C>[C:28]1([S:25]([NH:24][C@@H:10]([CH2:9][C:4]2[CH:5]=[CH:6][C:7]([OH:8])=[C:2]([NH:1][CH3:38])[CH:3]=2)[C:11]([NH:13][CH2:14][CH2:15][CH2:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[O:12])(=[O:27])=[O:26])[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1

Participants

6

Reactant 4

HCID 712FormaldehydeHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 69129795HCID 69129795, compound

Product 1

HCID 69129234HCID 69129234, compound

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

(2S)-3-(3-Amino-4-hydroxy-phenyl)-2-benzenesulfonylamino-N-(4-phenyl-butyl)-propionamide (502 mg, 1.07 mmol) is dissolved in dichloroethane (5 mL). 37% formaldehyde (120 mg, 1.47 mmol) and NaBH(OAc)3 (1.1 g, 5 mmol) are added. The mixture is stirred overnight. Saturated NaHCO3 (20 mL) is added and the crude mixture is extracted with ETOAC three times. The organic phase is dried and concentrated in vacuo. The small volume of solution is filtered through silica gel plug to provide a crude solution of (2S)-2-benzenesulfonylamino-3-(4-hydroxy-3-methylamino-phenyl)-N-(4-phenyl-butyl)-propionamide which is used without further purification.

Workup

  1. extractionthe crude mixture is extracted with ETOAC three times
  2. customThe organic phase is dried
  3. concentrationconcentrated in vacuo
  4. filtrationThe small volume of solution is filtered through silica gel plug

Sources & evidence

ORD record
ord-018d98ee059545d0a6dcb7fea31accef
Source dataset
uspto-grants-2003_07
Patent number
US06586467B2

Reaction notes

Loading…