Hydrochloric Acid → HCID 117628891, compound

HRID 2278374Notes

Reaction equation

HRID 2278374 reaction equation
Cl.[NH2:2][C@@H:3]([C:6]1[S:7][C:8]([CH:11]2[O:16]CC(C)(C)CO2)=[CH:9][CH:10]=1)[CH2:4][OH:5].C(N(CC)CC)C.C[Si](Cl)(C)C.[S:31]1[C:35]2[CH:36]=[C:37]([S:40](Cl)(=[O:42])=[O:41])[CH:38]=[CH:39][C:34]=2[N:33]=[CH:32]1.Cl>C(Cl)Cl.CO>[CH:11]([C:8]1[S:7][C:6]([C@H:3]([NH:2][S:40]([C:37]2[CH:38]=[CH:39][C:34]3[N:33]=[CH:32][S:31][C:35]=3[CH:36]=2)(=[O:41])=[O:42])[CH2:4][OH:5])=[CH:10][CH:9]=1)=[O:16]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 6397ChlorotrimethylsilaneHCID 8471TriethylamineHCID 27951701,3-Benzothiazole-6-sulfonyl chlorideHCID 117628857HCID 117628857, compound

Product 1

HCID 117628891HCID 117628891, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of (2R)-2-amino-2-[5-(5,5-dimethyl-1,3-dioxan-2-yl)thiophen-2-yl]ethanol hydrochloride (11.54 g, 39.3 mmol) in DCM (262 mL) at 0° C. was added slowly triethylamine (25 mL, 179 mmol). The mixture was stirred 15 minutes, after which TMSCl (5.52 mL, 43.2 mmol) was added. The mixture was stirred for 30 minutes at 0° C. and then 1,3-benzothiazole-6-sulfonyl chloride (9.64 g, 41.2 mmol) was added. The reaction mixture was allowed to reach room temperature overnight, and then 1N HCl (100 mL) and MeOH (50 mL) were added and the reaction mixture was stirred for 2 hours. The organic layer was separated and the aqueous layer was extracted 5 times with ethyl acetate (5×300 mL). The organic layers were combined and washed twice with a saturated solution of sodium bicarbonate (2×250 mL), then washed with brine (250 mL), dried over magnesium sulfate, filtered and concentrated under reduced pressure. The residue was swished with ether to obtain the pure desired product.

Workup

  1. stirringThe mixture was stirred for 30 minutes at 0° C.
  2. waitto reach room temperature overnight
  3. stirringthe reaction mixture was stirred for 2 hours
  4. customThe organic layer was separated
  5. extractionthe aqueous layer was extracted 5 times with ethyl acetate (5×300 mL)
  6. washwashed twice with a saturated solution of sodium bicarbonate (2×250 mL)
  7. washwashed with brine (250 mL)
  8. dry with materialdried over magnesium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-5cbda89482014ce2b144f82c659b062f
Source dataset
uspto-grants-2015_09
Patent number
US09133157B2

Reaction notes

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