Dicyclohexylcarbodiimide → L-Phenylalanine

HRID 1938626Notes

Reaction equation

HRID 1938626 reaction equation
Cl.[NH2:2][C@H:3]([C:11]([OH:13])=[O:12])[CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.C(N(C(C)C)CC)(C)C.N1NN=NC=1C1C=CC=CC=1C1C=CC2N(C(CCCCCC)C(O)=O)C=NC=2C=1.OC1C2N=NNC=2C=CC=1.C1(N=C=NC2CCCCC2)CCCCC1>>[NH2:2][C@H:3]([C:11]([OH:13])=[O:12])[CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1

Participants

6

Reactant 5

HCID 10868DicyclohexylcarbodiimideHCID 81531DiisopropylethylamineHCID 12000150L-Phenylalanine, hydrochloride (1:1)HCID 158381802-[5-[2-(2H-tetrazol-5-yl)phenyl]benzimidazol-1-yl]octanoic acidHCID 178418300HCID 178418300, compound

Product 1

HCID 6140L-Phenylalanine

Procedure

L-Phenylalanine hydrochloride (1.75 mmoles, 380 mg), diisopropylethylamine (1.93 mmoles, 0.34 ml), 2-[5-[2-(2H-tetrazol-5-yl)phenyl]-1H-benzimidazol-1-yl]octanoic acid (1.24 mmoles, 0.50 g), hydroxybenzotriazole (1.36 moles mg) and dicyclohexylcarbodiimide (1.36 mmoles, 280 mg) were reacted as in Example 37. The stereoisomers were separated by chromatography over silica gel eluted which 2% methanol in chloroform. The isomers were hydrolyzed as in Example 37 to yield N-[| -oxo-2-[5-[2-(2H-tetrazole-5-yl]phenyl]-1H-benzimidazol-1-yl]octyl]-L-phenylalanine. Isomer A: 187 mg (MS) M. Pt.: Dec. 165° C. Calculated for C31H33N7O3.0.9 HCl: C, 63.75; H, 5.85; N, 16.79. Found: C, 63.86; H, 6.00; N, 16.09. Isomer B: 80 mg (MS). M. Pt.: Dec. 160° C. Calculated for C31H33N7O3.0.89 HCl: C, 63.75; H, 5.85; N, 16.79. Found: C, 63.76; H, 5.85; N, 16.70.

Workup

  1. customThe stereoisomers were separated by chromatography over silica gel
  2. washeluted which 2% methanol in chloroform

Sources & evidence

ORD record
ord-6498415f07bd4efca10aba1eb5305225
Source dataset
uspto-grants-1997_12
Patent number
US05693633

Reaction notes

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