Potassium Hydroxide → (S)-2-amino-3-(phenyl-pyrimidin-2-ylamino)-propanoic acid amide

HRID 332928Notes

Reaction equation

C(OC([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]([NH2:12])=[O:11])=O)(C)(C)C.[OH-].[K+]>Cl>[NH2:8][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:16]=[CH:17][CH:18]=[CH:19][N:20]=1)[C:10]([NH2:12])=[O:11]

Participants

Conditions

Temperature: 5 °C

Procedure

(S)-2-tert-Butoxycarbonylamino-3-(phenyl-pyrimidin-2-ylamino)-propanoic acid amide (48.5 g, 136 mmol, >99.9% ee) is introduced at 40° C. in portions into hydrochloric acid (16% strength, 80 ml), and the resulting solution is stirred for 1 h at this temperature. After cooling to 5° C., the pH is adjUsted to 10 by adding concentrated potassium hydroxide solution. The precipitated solid is filtered off with suction and dried to give (S)-2-amino-3-(phenyl-pyrimidin-2-ylamino)-propanoic acid amide (35.3 g, 80% yield, 79% content, 99.8% ee) as a colorless solid, which can be further reacted or else crystallized again from aqueoUs solution, as desired.

Workup

filtrationThe precipitated solid is filtered off with suction
customdried

Sources & evidence

ORD record: ord-7468ad6c8bcd42888a6707c1e4755f38
Source dataset: uspto-grants-2014_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08877926B2

Reaction notes

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