Triethylamine → HCID 86698457, compound

HRID 527650Notes

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 190, 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-9d646950e74e4d7fb997e9cad468e62d
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09346790B2

Reaction notes

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