Sulfuric Acid → (S)-2-tert-butoxycarbonylamino-3-(phenyl-pyrimidin-2-ylamino)-propanoic acid

HRID 332926Notes

Reaction equation

HRID 332926 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:13][N:14]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[C:15]1[N:20]=[CH:19][CH:18]=[CH:17][N:16]=1)[C:10]([O-:12])=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].C1([C@@H]([NH3+])C)C=CC=CC=1.S(=O)(=O)(O)O>C(O)(C)C>[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:13][N:14]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[C:15]1[N:20]=[CH:19][CH:18]=[CH:17][N:16]=1)[C:10]([OH:12])=[O:11])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 1118Sulfuric AcidHCID 86692182(S)-1-phenylethyl-ammonium (S)-2-tert-butoxycarbonylamino-3-(phenyl-pyrimidin-2-ylamino)-propanoate

Product 1

HCID 56832947(S)-2-tert-butoxycarbonylamino-3-(phenyl-pyrimidin-2-ylamino)-propanoic acidYield 95.4%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A sUspension of (S)-1-phenylethyl-ammonium (S)-2-tert-butoxycarbonylamino-3-(phenyl-pyrimidin-2-ylamino)-propanoate (37.2 g, 77.5 mmol, 99.5% de) in aqueoUs isopropanol (50% strength, 90 ml) is admixed with 1N sulfuric acid (97 ml, 48.5 mmol) and stirred for 1 h at RT. The solid is filtered off with suction and dried to give (S)-2-tert-butoxycarbonylamino-3-(phenyl-pyrimidin-2-ylamino)-propanoic acid (26.5 g, 95%, >99.9% ee) as a colorless solid.

Workup

  1. filtrationThe solid is filtered off with suction
  2. customdried

Sources & evidence

ORD record
ord-f57b34e321654e658d2faf90d7bdc103
Source dataset
uspto-grants-2014_11
Patent number
US08877926B2

Reaction notes

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