Ethyl Acetate → N-(((3S,4R,5S)-3-(2,3-difluorophenyl)-4-(hydroxymethyl)-5-((trityloxy)methyl)tetrahydrofuran-3-yl)carbamothioyl)benzamide

HRID 707682Notes

Reaction equation

HRID 707682 reaction equation
[C:1]([N:9]=[C:10]=[S:11])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:12][C@@:13]1([C:41]2[CH:46]=[CH:45][CH:44]=[C:43]([F:47])[C:42]=2[F:48])[CH2:17][O:16][C@H:15]([CH2:18][O:19][C:20]([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C@H:14]1[CH2:39][OH:40].CCOC(C)=O>C(Cl)Cl>[F:48][C:42]1[C:43]([F:47])=[CH:44][CH:45]=[CH:46][C:41]=1[C@@:13]1([NH:12][C:10]([NH:9][C:1](=[O:8])[C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[S:11])[C@H:14]([CH2:39][OH:40])[C@@H:15]([CH2:18][O:19][C:20]([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)([C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)[C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[O:16][CH2:17]1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 68284Benzoyl isothiocyanateHCID 70556450HCID 70556450, compound

Product 1

HCID 60169626N-(((3S,4R,5S)-3-(2,3-difluorophenyl)-4-(hydroxymethyl)-5-((trityloxy)methyl)tetrahydrofuran-3-yl)carbamothioyl)benzamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Benzoyl isothiocyanate (6 g) was added dropwise to a solution containing ((2S,3R,4S)-4-amino-4-(2,3-difluorophenyl)-2-((trityloxy)methyl)tetrahydrofuran-3-yl)methanol, obtained in Preparation Example 1-(3), (15.42 g) in CH2Cl2 (80 mL), and the mixture was stirred at RT for 18 h. EtOAc was added and the mixture was extracted with NaHCO3 (3×100 mL), dried over MgSO4, evaporated, and the residue was purified by silica gel column chromatography (0% to 30% EtOAc in hexanes) to obtain the title compound (19.06 g). 1H-NMR (400 MHz, CDCl3) δ (ppm): 3.00 (t, J=6.2 Hz, 1H), 3.08-3.17 (m, 1H), 3.26 (dd, J=10.2, 4.2 Hz, 1H), 3.38 (dd, J=10.2, 3.9 Hz, 1H), 3.73-3.95 (m, 2H), 4.04-4.12 (m, 1H), 4.54 (d, J=9.6 Hz, 1H), 4.69 (d, J=9.9 Hz, 1H), 7.05-7.68 (m, 21H) 7.88 (d, J=7.1 Hz, 2H), 8.88 (s, 1H), 11.83 (s, 1H)

Workup

  1. extractionthe mixture was extracted with NaHCO3 (3×100 mL)
  2. dry with materialdried over MgSO4
  3. customevaporated
  4. customthe residue was purified by silica gel column chromatography (0% to 30% EtOAc in hexanes)

Sources & evidence

ORD record
ord-1ac0f9f9433242b3b28c40ef6de6df88
Source dataset
uspto-grants-2015_11
Patent number
US09175013B2

Reaction notes

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