Sulfuric Acid → (2S)-2-(Naphthalene-1-sulfonylamino)-3-(4-(2-(1,4,5,6-tetrahydropyrimidin-2-ylcarbamoyl)-ethyl)-benzoylamino)-propionic acid isobutyl ester

HRID 427324Notes

Reaction equation

HRID 427324 reaction equation
[C:1]1([S:11]([NH:14][C@@H:15]([CH2:19][NH:20][C:21](=[O:39])[C:22]2[CH:27]=[CH:26][C:25]([CH2:28][CH2:29][C:30](=[O:38])[NH:31][C:32]3[NH:33][CH2:34][CH2:35][CH2:36][N:37]=3)=[CH:24][CH:23]=2)[C:16]([OH:18])=[O:17])(=[O:13])=[O:12])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.S(=O)(=O)(O)O>C(O)C(C)C>[CH2:4]([O:17][C:16](=[O:18])[C@@H:15]([NH:14][S:11]([C:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1)(=[O:13])=[O:12])[CH2:19][NH:20][C:21](=[O:39])[C:22]1[CH:27]=[CH:26][C:25]([CH2:28][CH2:29][C:30](=[O:38])[NH:31][C:32]2[NH:37][CH2:36][CH2:35][CH2:34][N:33]=2)=[CH:24][CH:23]=1)[CH:5]([CH3:10])[CH3:6]

Participants

4

Reactant 2

HCID 1118Sulfuric AcidHCID 11135414(2S)-2-(naphthalene-1-sulfonylamino)-3-(4-(2-(1,4,5,6-tetrahydropyrimidin-2-ylcarbamoyl)-ethyl)-benzoylamino)-propionic acid

Product 1

HCID 57303081(2S)-2-(Naphthalene-1-sulfonylamino)-3-(4-(2-(1,4,5,6-tetrahydropyrimidin-2-ylcarbamoyl)-ethyl)-benzoylamino)-propionic acid isobutyl ester

Reagents, catalysts & solvents 1

HCID 6560IsobutanolSolvent

Procedure

600 mg of (2S)-2-(naphthalene-1-sulfonylamino)-3-(4-(2-(1,4,5,6-tetrahydropyrimidin-2-ylcarbamoyl)-ethyl)-benzoylamino)-propionic acid was dissolved in 12 ml of isobutanol and 0.1 ml of concentrated sulfuric acid was added. The reaction solution was boiled for 24 hours. The solvent was removed in vacuo, and the residue was chromatographed on silica gel eluting with dichloromethane/methanol/acetic acid/water (9/1/0.1/0.1). The product was dissolved in acetic acid/water and lyophilized. Yield 250 mg. MS (ES+): m/e=608.5 (M+H)+.

Workup

  1. customThe solvent was removed in vacuo
  2. customthe residue was chromatographed on silica gel eluting with dichloromethane/methanol/acetic acid/water (9/1/0.1/0.1)
  3. dissolutionThe product was dissolved in acetic acid/water

Sources & evidence

ORD record
ord-2f158fd2fc6042218c66b13e3877197a
Source dataset
uspto-grants-2001_11
Patent number
US06313119B1

Reaction notes

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