Triethylamine → HCID 86698457, compound

HRID 1484653Notes

Reaction equation

[CH3:1][C:2]1([CH3:20])[C:6]2[C:7]([O:12][C:13]3[N:18]=[CH:17][C:16]([NH2:19])=[CH:15][N:14]=3)=[CH:8][CH:9]=[C:10]([CH3:11])[C:5]=2[O:4][CH2:3]1.[CH3:21][C:22]([O:25][C:26]([NH:28][C@H:29]([CH2:33][CH3:34])[C:30](O)=[O:31])=[O:27])([CH3:24])[CH3:23].CCN(CC)CC.C(P1(=O)OP(CCC)(=O)OP(CCC)(=O)O1)CC>C(OCC)(=O)C>[CH3:1][C:2]1([CH3:20])[C:6]2[C:7]([O:12][C:13]3[N:14]=[CH:15][C:16]([NH:19][C:30]([C@H:29]([NH:28][C:26](=[O:27])[O:25][C:22]([CH3:24])([CH3:23])[CH3:21])[CH2:33][CH3:34])=[O:31])=[CH:17][N:18]=3)=[CH:8][CH:9]=[C:10]([CH3:11])[C:5]=2[O:4][CH2:3]1

Participants

Conditions

Temperature: 5 °C

Procedure

2-[(3,3,7-trimethyl-2,3-dihydro-1-benzofuran-4-yl)oxy]-5-pyrimidinamine (Intermediate 33, 220 mg, 0.81 mmol) was dissolved in ethyl acetate (10 mL) and of (2R)-2-({[(1,1-dimethylethyl)oxy]carbonyl}amino)butanoic acid (181.1 mg, 0.89 mmol) was added followed by the addition of Et3N (0.35 mL, 2.02 mmol). The resulting solution was cooled down to 5° C. and a solution of T3P 50% w/w in ethyl acetate (0.53 mL, 0.89 mmol) was added drop wise in 15 min. The reaction mixture was stirred for 30 min at 5° C. The reaction was quenched with water (50 mL) and ethyl acetate (50 mL), two phases were separated and the organic layer was dried over Na2SO4 and concentrated under vacuum. The residue was purified by flash chromatography on silica gel using cyclohexane/ethyl acetate 60:40 as eluent affording the title compound (213 mg).

Workup

additionwas added
customThe reaction was quenched with water (50 mL) and ethyl acetate (50 mL), two phases
customwere separated
dry with materialthe organic layer was dried over Na2SO4
concentrationconcentrated under vacuum
customThe residue was purified by flash chromatography on silica gel

Sources & evidence

ORD record: ord-b5036a07d2e84dd19d796ff943cb2314
Source dataset: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09422272B2

Reaction notes

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