Sodium → HCID 57378096, compound

HRID 1521883Notes

Reaction equation

HRID 1521883 reaction equation
C(OC([NH:8][C@H:9]([C:14]([O:16][CH2:17][N:18]1[C:22]([C:23]2[CH:28]=[CH:27][C:26]([O:29][C:30]([F:33])([F:32])[F:31])=[C:25]([Cl:34])[CH:24]=2)=[CH:21][S:20][C:19]1=[N:35][C:36](=[O:52])[CH2:37][C:38]1[C:46]2[C:45](=[O:47])[N:44]([CH3:48])[C:43](=[O:49])[N:42]([CH3:50])[C:41]=2[O:40][C:39]=1[CH3:51])=[O:15])[C@H:10]([CH2:12][CH3:13])[CH3:11])=O)(C)(C)C.[Na].ClC1C=C(C2N=C(NC(=O)CC3C4C(=O)N(C)C(=O)N(C)C=4OC=3C)SC=2)C=CC=1OC(F)(F)F>CC(C)=O>[ClH:34].[NH2:8][C@H:9]([C:14]([O:16][CH2:17][N:18]1[C:22]([C:23]2[CH:28]=[CH:27][C:26]([O:29][C:30]([F:33])([F:31])[F:32])=[C:25]([Cl:34])[CH:24]=2)=[CH:21][S:20][C:19]1=[N:35][C:36](=[O:52])[CH2:37][C:38]1[C:46]2[C:45](=[O:47])[N:44]([CH3:48])[C:43](=[O:49])[N:42]([CH3:50])[C:41]=2[O:40][C:39]=1[CH3:51])=[O:15])[C@H:10]([CH2:12][CH3:13])[CH3:11]

Participants

5

Reactant 3

HCID 5360545SodiumHCID 46918165HCID 46918165, compoundHCID 67984941HCID 67984941, compound

Product 1

HCID 57378096HCID 57378096, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

Step-1: [4-[3-Chloro-4-(trifluoromethoxy)phenyl]-2-{[(1,3,6-trimethyl-2,4-dioxo-1,2,3,4-tetrahydrofuro[2,3-d]pyrimidin-5-yl)acetyl]imino}-1,3-thiazol-3 (2H)-yl]methyl N-(tert-butoxycarbonyl)-L-isoleucinate: The title compound was prepared by the reaction of sodium salt of N-{4-[3-Chloro-4-(trifluoromethoxy)phenyl]-1,3-thiazol-2-yl}-2-(1,3,6-trimethyl-2,4-dioxo-1,2,3,4-tetrahydrofuro[2,3-d]pyrimidin-5-yl)acetamide (1.0 g, 0.0018 mol) in dry acetone (40 ml) with intermediate 6 (2.36 g, 0.0063 mol) in dry acetone (10 ml) to obtain 210 mg of product as a pale yellow solid. 1H NMR (300 MHz, CDCl3) δ 0.74 (t, J=7.5 Hz, 3H), 0.89 (d, J=6.9 Hz, 3H), 1.25 (s, 9H), 1.80-1.87 (m, 2H), 2.36 (s, 3H), 3.33 (s, 3H), 3.50-3.57 (m, 5H), 3.73 (s, 2H), 4.26-4.33 (m, 1H), 5.19 (d, J=9.0 Hz, 1H), 6.49 (d, J=12.2 Hz, 1H), 6.64 (d, J=11.7 Hz, 1H), 7.36 (d, J=8.1 Hz, 1H), 7.71-7.79 (m, 1H), 11.40 (br s, 1H); ESI-MS (m/z): 772.01 (M+H)+.

Sources & evidence

ORD record
ord-4b12fa1c2b1e4934889b21d2e1b083a0
Source dataset
uspto-grants-2015_07
Patent number
US09073955B2

Reaction notes

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