Acetic Anhydride → [(Z)-[1-amino-2-(8-phenyl-1,4-dioxaspiro[4.5]decan-8-yl)ethylidene]amino] acetate

HRID 2169301Notes

Reaction equation

HRID 2169301 reaction equation
[OH:1][NH:2][C:3](=[NH:21])[CH2:4][C:5]1([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH2:14][CH2:13][C:8]2([O:12][CH2:11][CH2:10][O:9]2)[CH2:7][CH2:6]1.[C:22](OC(=O)C)(=[O:24])[CH3:23].CCCCCC>C(OCC)(=O)C>[C:22]([O:1]/[N:2]=[C:3](\[NH2:21])/[CH2:4][C:5]1([C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH2:6][CH2:7][C:8]2([O:9][CH2:10][CH2:11][O:12]2)[CH2:13][CH2:14]1)(=[O:24])[CH3:23]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 8058HexaneHCID 178510734HCID 178510734, compound

Product 1

HCID 90271666[(Z)-[1-amino-2-(8-phenyl-1,4-dioxaspiro[4.5]decan-8-yl)ethylidene]amino] acetateYield 85.17%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

A mixture of N-hydroxy-2-(8-phenyl-1,4-dioxa-spiro[4.5]dec-8-yl)-acetamidine (266) (600 mg, 2.01 mmol) and acetic anhydride (2 mL) was stirred at room temperature for 16 h (TLC, ethyl acetate:hexane=7:3/UV/SiO2, Rf=0.4). The reaction mixture was diluted with ethyl acetate (50 mL), washed with water (2×25 mL), brine (25 mL), dried and concentrated in vacuo to get crude mass which was purified by CombiFlash using a gradient eluent mixture of ethyl acetate and hexane to get pure (Z)-(1-amino-2-{8-phenyl-1,4-dioxaspiro[4.5]decan-8-yl}ethylidene)amino acetate (267) (585 mg, 85.17%) as a white sticky solid.

Workup

  1. washwashed with water (2×25 mL), brine (25 mL)
  2. customdried
  3. concentrationconcentrated in vacuo
  4. customto get crude mass which
  5. customwas purified by CombiFlash
  6. additiona gradient eluent mixture of ethyl acetate and hexane

Sources & evidence

ORD record
ord-67ff78a65a3f4899b05f8b47a56ef583
Source dataset
uspto-grants-2015_06
Patent number
US09045486B2

Reaction notes

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