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

HRID 1295516Notes

Reaction equation

HRID 1295516 reaction equation
[F:1][C:2]([F:22])([F:21])C1C=C(C=CC=1)CCOC1C=CC([N+]([O-])=O)=CC=1.[F:23][C:24]([F:56])([F:55])[C:25]1[CH:26]=[C:27]([CH:52]=[CH:53][CH:54]=1)[CH2:28][CH2:29][O:30][C:31]1[CH:36]=[CH:35][C:34]([NH:37][C:38]([C@:40]([NH:44]C(=O)OC(C)(C)C)([CH3:43])[CH2:41][OH:42])=[O:39])=[CH:33][CH:32]=1.C(N[C@](C)(C(O)=O)CO)(OC(C)(C)C)=O.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[C:96](=[O:99])([O-:98])N>CCN(C(C)C)C(C)C>[F:1][C:2]([F:22])([F:21])[C:96]([OH:98])=[O:99].[F:23][C:24]([F:55])([F:56])[C:25]1[CH:26]=[C:27]([CH:52]=[CH:53][CH:54]=1)[CH2:28][CH2:29][O:30][C:31]1[CH:32]=[CH:33][C:34]([NH:37][C:38](=[O:39])[C@:40]([NH2:44])([CH3:43])[CH2:41][OH:42])=[CH:35][CH:36]=1

Participants

7

Reactant 5

HCID 276CarbamateHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 12991620(S)-2-((tert-Butoxycarbonyl)amino)-3-hydroxy-2-methylpropanoic acidHCID 691142091-(3-(Trifluoromethyl)phenethyloxy)-4-nitrobenzeneHCID 86605703tert-butyl (S)-2-(4-(3-(trifluoromethyl)phenethyloxy)phenylcarbamoyl)-1-hydroxypropan-2-ylcarbamate

Product 1

HCID 86605702(s)-n-(4-(3-(Trifluoromethyl)phenethyloxy)phenyl)-2-amino-3-hydroxy-2-methylpropanamide trifluoroacetic acid saltYield 47.9%

Reagents, catalysts & solvents 1

HCID 81531DiisopropylethylamineSolvent

Procedure

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).

Workup

  1. customprovided in Example 5(A)

Sources & evidence

ORD record
ord-fa1934915d204869886e459eb23d1be2
Source dataset
uspto-grants-2007_07
Patent number
US07241812B2

Reaction notes

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