Hydrochloric Acid → HCID 70605670, compound

HRID 2163826Notes

Reaction equation

HRID 2163826 reaction equation
[ClH:1].Cl.[NH2:3][CH:4]([CH:12]1[NH:16][CH:15]([C:17]([O:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[O:18])[C:14]2([CH2:31][CH2:30][O:29][CH2:28][CH2:27]2)[S:13]1)[C:5]([O:7]C(C)(C)C)=[O:6]>[N+](C)([O-])=O>[ClH:1].[NH2:3][CH:4]([CH:12]1[NH:16][CH:15]([C:17]([O:19][CH2:20][C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)=[O:18])[C:14]2([CH2:27][CH2:28][O:29][CH2:30][CH2:31]2)[S:13]1)[C:5]([OH:7])=[O:6]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 22749580HCID 22749580, compound

Product 1

HCID 70605670HCID 70605670, compoundYield 72.5%

Reagents, catalysts & solvents 1

HCID 6375NitromethaneSolvent

Conditions

Temperature
-5 °C

Procedure

Dry gaseous hydrogen chloride is bubbled into a suspension of 6.6 g (0.0144 mole) of tert-butyl alpha-amino-4-benzyloxycarbonyl-8-oxa-1-thia-3-azaspiro[4,5]decane-2-acetate hydrochloride in 150 ml of anhydrous nitromethane at 0° C. After 15 minutes, most of the product has dissolved and the bubbling of hydrogen chloride is continued for 1 hour. Insoluble material is filtered off and the nitromethane solution is degassed at a pressure of 20 mm Hg in a rotary evaporator at ambient temperature to eliminate as much gaseous hydrogen chloride as possible. 700 ml of anhydrous diethyl ether are added, followed by cooling to -5° C for 4 hours. In this way, a precipitate is obtained which is filtered off, washed with diethyl ether and dried in vacuo to give 4.2 g (0.0104 mole) of alpha-amino-4-benzyloxycarbonyl-8-oxa-1-thia-3-azaspiro[4.5]decane-2-acetic acid hydrochloride (yield: 72.5% of theory); M.P. 152-153° C.

Workup

  1. dissolutionmost of the product has dissolved
  2. customthe bubbling of hydrogen chloride
  3. waitis continued for 1 hour
  4. filtrationInsoluble material is filtered off
  5. customthe nitromethane solution is degassed at a pressure of 20 mm Hg in a rotary evaporator at ambient temperature
  6. addition700 ml of anhydrous diethyl ether are added
  7. customIn this way, a precipitate is obtained which
  8. filtrationis filtered off
  9. washwashed with diethyl ether
  10. customdried in vacuo

Sources & evidence

ORD record
ord-0a0b6ead26e34b01bf4f2be8dfa205cb
Source dataset
uspto-grants-1979_01
Patent number
US04137236

Reaction notes

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