Chlorotrimethylsilane → HCID 57462746, compound

HRID 1444585Notes

Reaction equation

C(OC([NH:8][C@@H:9]([CH3:21])[CH:10]([C:12]1[O:13][C:14]2[CH:20]=[CH:19][CH:18]=[CH:17][C:15]=2[N:16]=1)[OH:11])=O)(C)(C)C.[CH3:22][Si](C)(C)[Cl:24].C(OC(C)C)(C)C>C(O)(C)C>[ClH:24].[NH2:8][C@@H:9]([CH2:21][CH3:22])[CH:10]([C:12]1[O:13][C:14]2[CH:20]=[CH:19][CH:18]=[CH:17][C:15]=2[N:16]=1)[OH:11]

Participants

Conditions

Temperature: 50 °C

Procedure

To a solution of 2(S)-(tert-butoxycarbonyl)amino-1-benzoxazol-2-ylpropan-1-ol (26.3 g, 86 mmol) in isopropanol (118 mL) at 20-25° C. was added trimethylchlorosilane (1.4 eq). The solution was stirred for 5 h at 50° C. Concentration of the reaction mixture to 52 mL followed by addition of isopropyl ether (210 mL), filtration and drying under vacuum afforded 2(S)-amino-1-benzoxazol-2-yl-butan-1-ol hydrochloride salt as a grey solid (16.4 g; yield=79%; mixture of diastereomers.

Workup

customdrying under vacuum

Sources & evidence

ORD record: ord-edfc2e96d8aa4ccd8200ab244604cae3
Source dataset: uspto-grants-2010_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07662849B2

Reaction notes

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