Acetic Acid → HCID 57670737, compound

HRID 384533Notes

Reaction equation

HRID 384533 reaction equation
[CH2:1]1[CH:5]2[CH2:6][NH:7][CH2:8][CH:4]2[CH2:3][N:2]1[CH2:9][C:10]1[CH:25]=[CH:24][C:13]([O:14][C:15]2[S:16][C:17]3[CH:23]=[CH:22][CH:21]=[CH:20][C:18]=3[N:19]=2)=[CH:12][CH:11]=1.[CH3:26][O:27][C:28](=[O:37])[C:29]1[CH:34]=[CH:33][C:32]([CH:35]=O)=[CH:31][CH:30]=1.C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(Cl)Cl>[CH3:26][O:27][C:28](=[O:37])[C:29]1[CH:34]=[CH:33][C:32]([CH2:35][N:7]2[CH2:6][CH:5]3[CH:4]([CH2:3][N:2]([CH2:9][C:10]4[CH:11]=[CH:12][C:13]([O:14][C:15]5[S:16][C:17]6[CH:23]=[CH:22][CH:21]=[CH:20][C:18]=6[N:19]=5)=[CH:24][CH:25]=4)[CH2:1]3)[CH2:8]2)=[CH:31][CH:30]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 15294Methyl 4-FormylbenzoateHCID 5049666Sodium triacetoxyborohydrideHCID 42599086HCID 42599086, compound

Product 1

HCID 57670737HCID 57670737, compoundYield 19.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-[4-(hexahydro-pyrrolo[3,4-c]pyrrol-2-ylmethyl)-phenoxy]-benzothiazole (200 mg, 0.56 mmol) in CH2Cl2 (22 mL) was added 4-formyl-benzoic acid methyl ester (103 mg, 0.62 mmol) followed by the addition of acetic acid (28 μL, 0.48 mmol) then sodium triacetoxyborohydride (144 mg, 0.68 mmol). The reaction stirred at rt for 16 h. The reaction was then washed with satd. aq. NaHCO3 (2×20 mL). The organic layer was dried, filtered and concentrated. The resulting oil was purified by column chromatography (20% to 60% EtOAc in Hexanes) to afford the title compound (55 mg, 19%). MS (ESI): mass calcd. for C29H29N3O3S, 499.64; m/z found, 500.2 [M+H]+. 1H NMR (500 MHz, CDCl3): 8.01 (d, J=8.3 Hz, 2H), 7.76 (d, J=8.1 Hz, 1H), 7.47-7.38 (m, 1H), 7.35-7.26 (m, 4H), 7.68 (d, J=7.9 Hz, 4H), 3.92 (s, 4H), 3.65 (d, J=12.2 Hz, 4H), 2.71-2.60 (m, 3H), 2.38 (d, J=7.2 Hz, 4H), 1.27 (s, 2H).

Workup

  1. washThe reaction was then washed with satd
  2. customThe organic layer was dried
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe resulting oil was purified by column chromatography (20% to 60% EtOAc in Hexanes)

Sources & evidence

ORD record
ord-7fa75ec271f54745be449ef528e9d938
Source dataset
uspto-grants-2013_02
Patent number
US08367719B2

Reaction notes

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