Hydrochloric Acid → HCID 178447591, compound

HRID 1979959Notes

Reaction equation

HRID 1979959 reaction equation
[C:1]([O:7][CH2:8][Cl:9])(=[O:6])[C:2]([CH3:5])([CH3:4])[CH3:3].[Br-].[Na+].C(OC([NH:19][CH2:20][C@H:21]1[CH2:26][CH2:25][C@H:24]([C:27]([OH:29])=[O:28])[CH2:23][CH2:22]1)=O)(C)(C)C.C(N(CC)CC)C.Cl>CN(C)C=O.C(OCC)(=O)C.CCOCC>[ClH:9].[NH2:19][CH2:20][C@H:21]1[CH2:22][CH2:23][C@H:24]([C:27]([O:29][CH2:8][O:7][C:1](=[O:6])[C:2]([CH3:5])([CH3:4])[CH3:3])=[O:28])[CH2:25][CH2:26]1

Participants

9

Reactant 5

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 87885Chloromethyl pivalateHCID 253881Sodium BromideHCID 178453624HCID 178453624, compound

Product 1

HCID 178447591HCID 178447591, compound

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent2×HCID 8857Ethyl AcetateSolvent2×

Procedure

Chloromethyl pivalate (33.2 g; 0.22 mol) was added to a suspension of sodium bromide (22.4 g; 0,22 mol) in dimethylformamide. After 2 h a solution of trans-4-(tert.-butyloxycarbonylaminomethyl)cyclohexanecarboxylic acid in triethylamine (24 g; 0.24 mol) and dimethylformamide was added. The mixture was stirred overnight at room temperature. The solvent was distilled off and water (1 L) and dichloromethane was added. The organic layer was separated, washed, dried and evaporated to yield 55 g. This product was dissolved in ethyl acetate and cooled. A solution of hydrochloric acid in ethyl acetate was added. After 1 h ether was added. The precipitate was filtered, washed and dried to yield 30.2 g, m.p. 165° C. after crystallisation from acetone.

Workup

  1. distillationThe solvent was distilled off
  2. additionwater (1 L) and dichloromethane was added
  3. customThe organic layer was separated
  4. washwashed
  5. customdried
  6. customevaporated
  7. customto yield 55 g
  8. temperaturecooled
  9. filtrationThe precipitate was filtered
  10. washwashed
  11. customdried
  12. customto yield 30.2 g, m.p. 165° C.
  13. customafter crystallisation from acetone

Sources & evidence

ORD record
ord-516bd06c75b64118a08de82a2ad0ba85
Source dataset
uspto-grants-1984_11
Patent number
US04483867

Reaction notes

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