Hydrochloric Acid → HCID 11188931, compound

HRID 1993024Notes

Reaction equation

HRID 1993024 reaction equation
C[O:2][C:3](=[O:30])[CH2:4][C@@H:5]([C:9]1[CH:14]=[CH:13][C:12]([O:15][CH2:16][C:17]2[S:21][C:20]([C:22]3[CH:27]=[CH:26][C:25]([CH3:28])=[CH:24][CH:23]=3)=[N:19][C:18]=2[CH3:29])=[CH:11][CH:10]=1)[C:6]#[C:7][CH3:8].Cl>C1COCC1.CO>[CH3:29][C:18]1[N:19]=[C:20]([C:22]2[CH:23]=[CH:24][C:25]([CH3:28])=[CH:26][CH:27]=2)[S:21][C:17]=1[CH2:16][O:15][C:12]1[CH:11]=[CH:10][C:9]([C@@H:5]([C:6]#[C:7][CH3:8])[CH2:4][C:3]([OH:30])=[O:2])=[CH:14][CH:13]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 59132738HCID 59132738, compound

Product 1

HCID 11188931HCID 11188931, compound

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

Ester 3.2 was dissolved in THF/MeOH/10% NaOH(aq) (1:1:1) solution (15 mL). After stirring at room temperature over 30 minutes, the mixture was acidified with 1N HCl (aq.) until pH=4. The aqueous phase was extracted with ethyl acetate and the combined organic phases were dried over Na2SO4 and concentrated. The crude residue was triturated with 20% ethyl acetate in hexanes (20 mL). The precipitate was filtered and compound 3 was acquired as a pale yellow powder (315 mg, 0.8 mmol). MS ESI m/e: 406 (M−H). 1H NMR (500 MHz) (CDCl3) δ 7.86 (2H, d, J=7.5 Hz); 7.36 (2H, d, J=9 Hz); 7.26 (2H, d, J=8 Hz); 6.96 (2H, d, J=8.5 Hz); 5.18 (2H, s); 4.1 (1H, m); 2.77 (2H, m); 2.52 (3H, s); 2.43 (3H, s); 1.86 (3H, s).

Workup

  1. extractionThe aqueous phase was extracted with ethyl acetate
  2. dry with materialthe combined organic phases were dried over Na2SO4
  3. concentrationconcentrated
  4. customThe crude residue was triturated with 20% ethyl acetate in hexanes (20 mL)
  5. filtrationThe precipitate was filtered

Sources & evidence

ORD record
ord-f66c87efe6824255a591fa5629d393ce
Source dataset
uspto-grants-2010_01
Patent number
US07649110B2

Reaction notes

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