Hydrochloric Acid → HCID 131723265, compound

HRID 2185948Notes

Reaction equation

HRID 2185948 reaction equation
[CH2:1]([C:3]1[S:4][CH:5]=[C:6]([C:8]2[CH:20]=[CH:19][C:11]([CH2:12][C@@H:13]([C:15]([O:17]C)=[O:16])[NH2:14])=[CH:10][CH:9]=2)[N:7]=1)[CH3:2].[OH-].[Na+].Cl>CO>[CH2:1]([C:3]1[S:4][CH:5]=[C:6]([C:8]2[CH:9]=[CH:10][C:11]([CH2:12][C@@H:13]([C:15]([OH:17])=[O:16])[NH2:14])=[CH:19][CH:20]=2)[N:7]=1)[CH3:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 131723266HCID 131723266, compound

Product 1

HCID 131723265HCID 131723265, compoundYield 136.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

N-(N-(BOC)-3-phenylsulfonyl)-nipecotyl)-(L)-4-(2-ethyl-4-thiazolyl)-phenylalanine, methyl ester (60 mg, 0.0925 mmol) was dissolved in 2.5 mL of MeOH and treated with 280 μL of 0.5 N NaOH. The reaction mixture was stirred overnight, acidified to pH=2-3 with 1.2 N HCl, and concentrated under vacuo to give a white solid. This solid was purified by preparative TLC on silica gel eluted with CH2Cl2:MeOH:AcOH (v/v/v 95:5:0.5) to afford N-(N-(BOC)-3-phenylsulfonyl)-nipecotyl)-(L)-4-(2-ethyl-4-thiazolyl)phenylalanine (34.9 mg).

Workup

  1. concentrationconcentrated under vacuo
  2. customto give a white solid
  3. customThis solid was purified by preparative TLC on silica gel
  4. washeluted with CH2Cl2

Sources & evidence

ORD record
ord-665558d78a3d4d30b0d6fd26e91d3fa1
Source dataset
uspto-grants-2002_06
Patent number
US06403584B1

Reaction notes

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