Diisopropyl Ether → HCID 18610516, compound

HRID 256081Notes

Reaction equation

HRID 256081 reaction equation
[NH2:1][C@H:2]1[CH2:8][S:7][CH:6]([C:9]2[S:10][CH:11]=[CH:12][CH:13]=2)[CH2:5][NH:4][C:3]1=[O:14].C(OC(N1[C:24](=[O:25])[C:23]2=[CH:26][CH:27]=[CH:28][CH:29]=[C:22]2[C:21]1=[O:30])=O)C.C(=O)(O)[O-].[Na+].C(OC(C)C)(C)C>CN(C)C=O.C(OCC)(=O)C.O>[O:14]=[C:3]1[C@@H:2]([N:1]2[C:24](=[O:25])[C:23]3=[CH:26][CH:27]=[CH:28][CH:29]=[C:22]3[C:21]2=[O:30])[CH2:8][S:7][CH:6]([C:9]2[S:10][CH:11]=[CH:12][CH:13]=2)[CH2:5][NH:4]1

Participants

8

Reactant 4

HCID 7914Diisopropyl EtherHCID 31187N-CarbethoxyphthalimideHCID 516892Sodium BicarbonateHCID 13854087HCID 13854087, compound

Product 1

HCID 18610516HCID 18610516, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

19.1 g of 6(R)-amino-5-oxo-2-(2-thienyl)perhydro-1,4-thiazepine [prepared as described in step (d) above], 18 g of N-ethoxycarbonylphthalimide and 29 g of sodium bicarbonate were suspended in 150 ml of dimethylformamide. The suspension was stirred for 7 hours at 60° C. and then left standing overnight at room temperature. At the end of this time, 500 ml of water, 100 ml of diisopropyl ether and 20 ml of ethyl acetate were added, and the mixture was stirred to precipitate the title compound. This was collected by filtration, and washed with water and with a 5:1 by volume mixture of diisopropyl ether and ethyl acetate, giving 27.4 of the title compound, melting at 246°-247.5° C. (with coloration).

Workup

  1. waitleft
  2. waitstanding overnight at room temperature
  3. stirringthe mixture was stirred
  4. customto precipitate the title compound
  5. filtrationThis was collected by filtration
  6. washwashed with water and with a 5:1 by volume mixture of diisopropyl ether and ethyl acetate

Sources & evidence

ORD record
ord-3aa500fcd5eb48c899f5be5aac323778
Source dataset
uspto-grants-1987_10
Patent number
US04699905

Reaction notes

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