Formic Acid → HCID 68115412, compound

HRID 1503899Notes

Reaction equation

HRID 1503899 reaction equation
[OH:1][CH2:2][CH2:3][C@@H:4]1[CH2:15][CH2:14][C:13]2[S:12][C:11]3[C:6](=[C:7]([O:16][CH:17]4[CH2:22][CH2:21][CH:20]([NH:23][C:24](=O)OC(C)(C)C)[CH2:19][CH2:18]4)[N:8]=[CH:9][N:10]=3)[C:5]1=2.C=O.[CH:33](O)=O>CO>[CH3:33][N:23]([CH3:24])[CH:20]1[CH2:19][CH2:18][CH:17]([O:16][C:7]2[N:8]=[CH:9][N:10]=[C:11]3[C:6]=2[C:5]2[C@H:4]([CH2:3][CH2:2][OH:1])[CH2:15][CH2:14][C:13]=2[S:12]3)[CH2:22][CH2:21]1

Participants

5

Reactant 3

HCID 284Formic AcidHCID 712FormaldehydeHCID 68115513HCID 68115513, compound

Product 1

HCID 68115412HCID 68115412, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
100 °C

Procedure

To a 25-mL round-bottom flask containing a solution of 16.5 (100 mg, 0.23 mmol, 1.00 equiv) in methanol (5 mL) was added HCHO (37%, 1 mL) and HCOOH (5 mL) at room temperature under nitrogen. The resulting solution was stirred overnight at 100° C. and evaporated under reduced pressure. The crude product (80 mg) was purified by preparative HPLC(SHIMADZU) under the following conditions: column: SunFire Prep C18, 19*150 mm 5 um; mobile phase: water (0.05% NH4HCO3) and CH3CN (start at 7.0% CH3CN then ramp up to 63.0% in 13 min); UV detection at 254 and 220 nm. The product-containing fractions were collected and the solvents evaporated to afford Compound I-33 (8 mg) as a colorless oil. An ee of 100% was measured by chiral-SFC analysis. 1H NMR (300 MHz, CDCl3) δ 7.26 (s, 1H), 5.24 (m, 1H), 3.72 (t, 1H), 3.47 (m, 1H), 3.08 (m, 2H), 2.70 (m, 1H), 2.03-2.68 (m, 11H), 1.25-1.81 (m, 9H). MS: m/z 362 (M+H)+.

Workup

  1. customevaporated under reduced pressure
  2. customThe crude product (80 mg) was purified by preparative HPLC(SHIMADZU) under the following conditions
  3. waitthen ramp up to 63.0% in 13 min
  4. customThe product-containing fractions were collected
  5. customthe solvents evaporated
  6. customto afford Compound

Sources & evidence

ORD record
ord-fa7c17b46f3641dda396c42212916148
Source dataset
uspto-grants-2015_12
Patent number
US09212190B2

Reaction notes

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