Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1) → tert-butyl (S)-2-(4-(4-(thiophen-2-yl)butoxy)phenylcarbamoyl)-1-hydroxypropan-2-ylcarbamate

HRID 1295515Notes

Reaction equation

HRID 1295515 reaction equation
[N+:1]([C:4]1[CH:19]=[CH:18][C:7]([O:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13]2[S:14][CH:15]=[CH:16][CH:17]=2)=[CH:6][CH:5]=1)([O-])=O.[C:20]([NH:27][C@:28]([CH3:34])([C:31](O)=[O:32])[CH2:29][OH:30])([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CCN(C(C)C)C(C)C>[S:14]1[CH:15]=[CH:16][CH:17]=[C:13]1[CH2:12][CH2:11][CH2:10][CH2:9][O:8][C:7]1[CH:18]=[CH:19][C:4]([NH:1][C:29]([C@:28]([NH:27][C:20](=[O:21])[O:22][C:23]([CH3:26])([CH3:25])[CH3:24])([CH3:34])[CH2:31][OH:32])=[O:30])=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 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 692655942-(4-(4-Nitrophenoxy)butyl)thiophene

Product 1

HCID 86605701tert-butyl (S)-2-(4-(4-(thiophen-2-yl)butoxy)phenylcarbamoyl)-1-hydroxypropan-2-ylcarbamateYield 66.8%

Reagents, catalysts & solvents 1

HCID 81531DiisopropylethylamineSolvent

Procedure

This compound was synthesized from 2-(4-(4-nitrophenoxy)butyl)thiophene (280 mg), N-(Boc)-α-methylserine (205 mg), HATU (442 mg), and DIPEA (506 μl) following the procedure described in Example 5(A) to yield 280 mg product (62% yield). 1H NMR (400 MHz, DMSO-d6) δ 9.24 (s, 1H), 7.44 (m, 2H), 7.29 (m, 1H), 6.9 (m, 1H), 6.84–6.81 (m, 3H), 5.00 (t, 1H), 3.93 (t, 2H), 3.61 (m, 2H), 2.84 (t, 2H), 1.73 (m, 4H), 1.48 (overlapping singlets, 9H).

Sources & evidence

ORD record
ord-74ce8fb06cb84b84b4fe22e91fd0bd34
Source dataset
uspto-grants-2007_07
Patent number
US07241812B2

Reaction notes

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