Carbamate → (s)-n-(4-(3-(Trifluoromethyl)phenethyloxy)phenyl)-2-amino-3-hydroxy-2-methylpropanamide trifluoroacetic acid salt

Participants

Role	Name	HCID	Charge
Reactant	Carbamate	HCID 276	—
Reactant	Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)	HCID 9886157	—
Reactant	(S)-2-((tert-Butoxycarbonyl)amino)-3-hydroxy-2-methylpropanoic acid	HCID 12991620	—
Reactant	1-(3-(Trifluoromethyl)phenethyloxy)-4-nitrobenzene	HCID 69114209	—
Reactant	tert-butyl (S)-2-(4-(3-(trifluoromethyl)phenethyloxy)phenylcarbamoyl)-1-hydroxypropan-2-ylcarbamate	HCID 86605703	—
Solvent	Diisopropylethylamine	HCID 81531	—
Product	(s)-n-(4-(3-(Trifluoromethyl)phenethyloxy)phenyl)-2-amino-3-hydroxy-2-methylpropanamide trifluoroacetic acid salt	HCID 86605702	47.9%

Reaction Steps

1-(3-(trifluoromethyl)phenethyloxy)-4-nitrobenzene (470 mg) was converted to 290 mg tert-butyl (S)-2-(4-(3-(trifluoromethyl)phenethyloxy)phenylcarbamoyl)-1-hydroxypropan-2-ylcarbamate following the general procedure provided in Example 5(A) employing N-(Boc)-α-methylserine (210 mg), HATU (360 mg), and DIPEA (900 μl). MS (ESI, M+H+)=483.4. The carbamate (145 mg) was deprotected following the procedure in Example 5(A) yielding 143 mg of the title compound. MS (ESI, M+H+)=383.1. 1H NMR (400 MHz, DMSO-d6) δ 9.8 (bs, 1H), 7.67–7.40 (m, 6H), 6.88 (m, 2H), 5.67 (bs, 1H), 4.18 (t, 3H), 3.91 (m, 1H), 3.58 (m, 1H), 3.11 (t, 3H), 1.41 (s, 3H).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07241812B2
Source dataset	uspto-grants-2007_07
ORD ID	ord-fa1934915d204869886e459eb23d1be2
Source note	uspto-grants-2007_07