Ethanol → HCID 20612419, compound

HRID 1990920Notes

Reaction equation

[C:1]([O:5][C:6]([N:8]1[C:12]2[N:13]=[C:14]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[N:15]=[C:16]([Cl:17])[C:11]=2[CH:10]=[C:9]1[CH2:24]Br)=[O:7])([CH3:4])([CH3:3])[CH3:2].CC[OH:28]>CS(C)=O.O>[C:1]([O:5][C:6]([N:8]1[C:12]2[N:13]=[C:14]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[N:15]=[C:16]([Cl:17])[C:11]=2[CH:10]=[C:9]1[CH:24]=[O:28])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 48 °C

Procedure

A suspension of the bromide 7 (2.00 g, 4.73 mmol), Na2HPO4 (806 mg, 5.68 mmol) and NaH2PO4 (227 mg, 1.89 mmol) in DMSO (50 mL) is heated under nitrogen to 48° C. After 1 h, all solids are dissolved, and the reaction is continued for 2 h. The solution is then poured in H2O (600 mL), and the mixture is extracted with EtOAc (2×150 mL). The combined EtOAc layers are washed with H2O (3×400 mL) and brine and dried over MgSO4. Filtration and concentration yields a yellow solid, which is triturated with EtOH giving 1.06 g (2.97 mmol, 63%) of the title compound as a yellow solid. MS (ES): m/z 304.7/306.7 (33/10) [MH+-Boc-H2O+2 MeOH], 272.7/274.7 (100/32) [MH+-Boc-H2O+MeOH]. 1H NMR (200 MHz, CDCl3): δ=1.79 (s, 9H), 7.44 (s, 1H), 7.48-7.55 (m, 3H), 8.51-8.60 (m, 2H), 10.39 (s, 1H). tR (method A)=10.4 min.

Workup

dissolutionall solids are dissolved
waitthe reaction is continued for 2 h
extractionthe mixture is extracted with EtOAc (2×150 mL)
washThe combined EtOAc layers are washed with H2O (3×400 mL) and brine
dry with materialdried over MgSO4
filtrationFiltration and concentration
customyields a yellow solid, which

Sources & evidence

ORD record: ord-991e3d6323dc48a99e010d2e7a171151
Source dataset: uspto-grants-2010_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07645754B2

Reaction notes

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