Glycine, N-(2,2-difluoroethyl)-, ethyl ester → (S)-ethyl 2-((3-(4-((4-(1-acetoxyhexan-3-ylamino)-2-amino-6-methylpyrimidin-5-yl)methyl)-3-methoxyphenoxy)propyl)(2,2-difluoroethyl)amino)acetate

HRID 2207098Notes

Reaction equation

HRID 2207098 reaction equation
[C:1]([O:4][CH2:5][CH2:6][C@@H:7]([NH:11][C:12]1[C:17]([CH2:18][C:19]2[CH:24]=[CH:23][C:22]([O:25][CH2:26][CH2:27][CH2:28]OS(C)(=O)=O)=[CH:21][C:20]=2[O:34][CH3:35])=[C:16]([CH3:36])[N:15]=[C:14]([NH2:37])[N:13]=1)[CH2:8][CH2:9][CH3:10])(=[O:3])[CH3:2].[F:38][CH:39]([F:48])[CH2:40][NH:41][CH2:42][C:43]([O:45][CH2:46][CH3:47])=[O:44]>>[C:1]([O:4][CH2:5][CH2:6][C@@H:7]([NH:11][C:12]1[C:17]([CH2:18][C:19]2[CH:24]=[CH:23][C:22]([O:25][CH2:26][CH2:27][CH2:28][N:41]([CH2:40][CH:39]([F:38])[F:48])[CH2:42][C:43]([O:45][CH2:46][CH3:47])=[O:44])=[CH:21][C:20]=2[O:34][CH3:35])=[C:16]([CH3:36])[N:15]=[C:14]([NH2:37])[N:13]=1)[CH2:8][CH2:9][CH3:10])(=[O:3])[CH3:2]

Participants

3

Reactant 2

HCID 60921893Glycine, N-(2,2-difluoroethyl)-, ethyl esterHCID 89906963(S)-3-(2-amino-5-(2-methoxy-4-(3-(methylsulfonyloxy)propoxy)benzyl)-6-methylpyrimidin-4-ylamino)hexyl acetate

Product 1

HCID 118000981(S)-ethyl 2-((3-(4-((4-(1-acetoxyhexan-3-ylamino)-2-amino-6-methylpyrimidin-5-yl)methyl)-3-methoxyphenoxy)propyl)(2,2-difluoroethyl)amino)acetateYield 51.8%

Procedure

The sub-title compound was synthesized by the method of example 9 step (vi) from the product of example 9 step (v) (75 mg) and the product of example 3 step (i) (112 mg). The sub-title compound (44 mg) was obtained as a pale yellow oil; 1H NMR (300 MHz, CDCl3); 6.81 (1H, d), 6.44 (1H, d), 6.37 (1H, dd), 5.77 (1H, tt), 4.97 (2H, br s), 4.28-4.09 (3H, m), 4.00-3.85 (4H, m), 3.86 (3H, s), 3.58 (2H, s), 3.45 (2H, s), 3.11-2.86 (4H, m), 2.36 (3H, s), 1.97 (3H, s), 1.95-1.74 (3H, m), 1.63-1.50 (1H, m), 1.46-1.33 (1H, m), 1.30-1.15 (5H, m), 1.12-0.98 (2H, m), 0.77 (3H, t); LC-MS: m/z 610.

Sources & evidence

ORD record
ord-d4abbdf983f14ddfbf5818e2035676f0
Source dataset
uspto-grants-2016_06
Patent number
US09376398B2

Reaction notes

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