L-Valine → HCID 131716562, compound

HRID 1032248Notes

Reaction equation

HRID 1032248 reaction equation
[CH:1]([NH2:14])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH:15]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[C@H:16]([C:20]([OH:22])=[O:21])[CH:17]([CH3:19])[CH3:18].C1(N=C=NC2CCCCC2)CCCCC1.N[C@H](C(O)=O)C(C)C>C(Cl)Cl>[NH:15]([C:23]([O:25][C:26]([CH3:28])([CH3:27])[CH3:29])=[O:24])[C@H:16]([C:20]([OH:22])=[O:21])[CH:17]([CH3:19])[CH3:18].[CH:1]([NH2:14])([C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 6287L-ValineHCID 7036BenzhydrylamineHCID 10868DicyclohexylcarbodiimideHCID 83693Boc-L-Valine

Product 1

HCID 131716562HCID 131716562, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Benzhydrylamine-resin (BHA) (5.0 g, 0.5-0.7 meg/g) was coupled with Boc-Val-OH (3.04 g, 14 mmol) in CH2Cl2 (25 mL) with dicyclohexylcarbodiimide (DCC) (2.88 g) for 18 hrs. The resultant BOC-Val-BHA-resin was washed with CH2Cl2 (2×75 mL), DMF (1×75 mL), MeOH (2×75 mL), CH2Cl2 (2×75 mL) and dried. An aliquot was hydrolyzed (1 mL of 6M propionic-HCl at 130° for 2 hours). Amino acid analysis showed a substitution of 0.33 mmol of Val per gram of resin. The remaining amino groups were acetylated with AC2O-pyridine, yield: 5.36 g.

Workup

  1. washThe resultant BOC-Val-BHA-resin was washed with CH2Cl2 (2×75 mL), DMF (1×75 mL), MeOH (2×75 mL), CH2Cl2 (2×75 mL)
  2. customdried
  3. custom(1 mL of 6M propionic-HCl at 130° for 2 hours)

Sources & evidence

ORD record
ord-91568478f6184b7ba61945f567cc2f99
Source dataset
uspto-grants-1990_09
Patent number
US04957737

Reaction notes

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