Hydrochloric Acid → HCID 22749592, compound

HRID 2163827Notes

Reaction equation

HRID 2163827 reaction equation
O.NN.[CH2:4]([O:11][C:12]([CH:14]1[C:18]2([CH2:23][CH2:22][S:21][CH2:20][CH2:19]2)[S:17][CH:16]([CH:24]([N:32]2C(=O)C3=CC=CC=C3C2=O)[C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[NH:15]1)=[O:13])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.[ClH:43]>CN(C)C=O>[ClH:43].[NH2:32][CH:24]([CH:16]1[NH:15][CH:14]([C:12]([O:11][CH2:4][C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=2)=[O:13])[C:18]2([CH2:19][CH2:20][S:21][CH2:22][CH2:23]2)[S:17]1)[C:25]([O:27][C:28]([CH3:30])([CH3:31])[CH3:29])=[O:26]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 24654Hydrazine hydrate (1:1)HCID 22749577HCID 22749577, compound

Product 1

HCID 22749592HCID 22749592, compoundYield 91.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

151.5 ml of a solution of dimethylforamide containing 2 moles per liter of hydrazine hydrate (0.3025 mole) are added, between 0 and 5° C, to a suspension of 156.3 g (0.275 mole) of tert-butyl 4-benzyloxycarbonyl-alpha-phthalimido-1,8-dithia-3-azaspiro[4.5]decane-2-acetate in 170 ml of anhydrous dimethylformamide. The addition is carried out over 75 minutes and is accompanied by a complete dissolution of the product. The reaction mixture is allowed to return to ambient temperature over a period of 1 hour, whereafter 309 ml of 1N hydrochloric acid are added dropwise at 20 to 25° C. The precipitate of phthaloghydrazide formed is filtered off and the mother liquors are evaporated to dryness. The residue is taken up in methanol and is precipitated with diethyl ether. In this way, there are obtained 119.1 g of tert-butyl alpha-amino-4-benzyloxycarbonyl-1,8-dithia-3-azaspiro[4.5]decane-2-acetate hydrochloride (yield 91.5% of theory); M.P. 178-181° C.

Workup

  1. additionThe addition
  2. dissolutionis accompanied by a complete dissolution of the product
  3. additionare added dropwise at 20 to 25° C
  4. customThe precipitate of phthaloghydrazide formed
  5. filtrationis filtered off
  6. customthe mother liquors are evaporated to dryness
  7. customis precipitated with diethyl ether

Sources & evidence

ORD record
ord-55ea9acaf4454d3b9660479f9394e536
Source dataset
uspto-grants-1979_01
Patent number
US04137236

Reaction notes

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