Hydrochloric Acid → HCID 58988191, compound

HRID 1807646Notes

Reaction equation

HRID 1807646 reaction equation
[Li+].C[Si]([N-][Si](C)(C)C)(C)C.[O:11]=[C:12]1[C:20]2[S:19][C:18]([NH:21][C:22](=[O:24])[CH3:23])=[N:17][C:16]=2[CH2:15][CH2:14][CH2:13]1.[CH:25](OC)=[O:26].Cl>C1COCC1>[CH:25]([CH:13]1[CH2:14][CH2:15][C:16]2[N:17]=[C:18]([NH:21][C:22](=[O:24])[CH3:23])[S:19][C:20]=2[C:12]1=[O:11])=[O:26]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7865Methyl formateHCID 597793N-(7-Oxo-4,5,6,7-tetrahydro-1,3-benzothiazol-2-yl)acetamideHCID 2733832Lithium Hexamethyldisilazide

Product 1

HCID 58988191HCID 58988191, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

LiHMDS solution (1 M, 27.7 mL) was added over 10 min to a suspension of N-(7-oxo-4,5,6,7-tetrahydro-benzothiazol-2-yl)-acetamide (Stage A.5, 2.0 g, 9.23 mmol) in dry THF (20 mL) cooled at −78° C. under an argon atm. The RM was then stirred at −78° C. for 2.5 h and methyl formate (2.308 mL, 36.9 mmol) added dropwise over 30 min. The RM was then warmed slowly to rt and was then stirred 18 h at rt. The RM was drown out into aqueous 1 M HCl (70 mL) and extracted 3× with DCM, dried over Na2SO4 and evaporated to give a the title compound as a solid. HPLC: tR 3.65 min (method D). MS: M−H=237. 1H-NMR in DMSO-d6 (400 MHz): 12.50 (s, br, 1H); 7.55 (s, 1H); 2.90-2.60 (m, 4H); 2.15 (s, 3H).

Workup

  1. temperatureThe RM was then warmed slowly to rt
  2. stirringwas then stirred 18 h at rt
  3. extractionextracted 3× with DCM
  4. dry with materialdried over Na2SO4
  5. customevaporated

Sources & evidence

ORD record
ord-6c8e39939ae7432f9ca1830da1b98695
Source dataset
uspto-grants-2013_01
Patent number
US08357707B2

Reaction notes

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