Acetic Acid → HCID 58746678, compound

HRID 724670Notes

Reaction equation

HRID 724670 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:14][C:15]1[CH:20]=[CH:19][C:18]([C:21]2[S:25](=[O:27])(=[O:26])[N:24]([C:28]([CH3:31])([CH3:30])[CH3:29])[C:23](=[O:32])[CH:22]=2)=[C:17]([Cl:33])[CH:16]=1)[C:10]([O:12][CH3:13])=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].[BH4-].[Li+].C(O)(=O)C>O1CCCC1.C(OCC)(=O)C>[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:14][C:15]1[CH:20]=[CH:19][C:18]([CH:21]2[S:25](=[O:26])(=[O:27])[N:24]([C:28]([CH3:31])([CH3:30])[CH3:29])[C:23](=[O:32])[CH2:22]2)=[C:17]([Cl:33])[CH:16]=1)[C:10]([O:12][CH3:13])=[O:11])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 4148881Lithium borohydrideHCID 11605762Methyl (2S)-2-[(tert-butoxycarbonyl)amino]-3-[4-(2-tert-butyl-1,1-dioxido-3-oxo-2,3-dihydroisothiazol-5-yl)-3-chlorophenyl]propanoate

Product 1

HCID 58746678HCID 58746678, compoundYield 54%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

Methyl (2S)-2-[(tert-butoxycarbonyl)amino]-3-[4-(2-tert-butyl-1,1-dioxido-3-oxo-2,3-dihydroisothiazol-5-yl)-3-chlorophenyl]propanoate (300 mg, 0.598 mmol) in tetrahydrofuran (6.00 mL) was cooled to 0° C. and treated with lithium tetrahydroborate solution in tetrahydrofuran (2.0 M, 0.329 mL). The reaction was allowed to stir for 0.5 h at rt. After addition of acetic acid (0.5 mL), the solution was diluted with ethyl acetate (100 mL), washed with water (100 mL), separated, dried over sodium sulfate, filtered and was concentrated in vacuo. The crude material was purified by silica gel chromatography (5–30% ethyl acetate/hexanes) to afford the product as a white solid (162 mg, 54%). 1H NMR (400 MHz, CD3OD): δ 7.45–7.42 (m, 2H), 7.31–7.27 (m, 1H), 5.59 (t, J=8.0 Hz, 1H), 4.39–4.36 (m, 1H), 3.70 (s, 3H), 3.38–3.33 (m, 1H), 3.25–3.14 (m, 2H), 2.95–2.92 (m, 1H), 1.67 (s, 9H), 1.37 (s, 9H); LCMS found for C17H24ClN2O5S (M+H)+: m/z=403.

Workup

  1. washwashed with water (100 mL)
  2. customseparated
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationwas concentrated in vacuo
  6. customThe crude material was purified by silica gel chromatography (5–30% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-1d5c28152564406ea3cb99a667e08a58
Source dataset
uspto-grants-2006_11
Patent number
US07141596B2

Reaction notes

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