Diisopropylethylamine → HCID 86656441, compound

HRID 69911Notes

Reaction equation

HRID 69911 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]1[CH2:14][NH:13][CH2:12][C@@H:11]([C:15]([OH:17])=[O:16])[CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].CCN(C(C)C)C(C)C.[CH2:27]([O:34][C:35](ON1C(=O)CCC1=O)=[O:36])[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1>ClCCl>[CH2:27]([O:34][C:35]([N:13]1[CH2:14][C@H:9]([NH:8][C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:7])[CH2:10][C@H:11]([C:15]([OH:17])=[O:16])[CH2:12]1)=[O:36])[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 83172Benzyl succinimido carbonateHCID 71601477HCID 71601477, compound

Product 1

HCID 86656441HCID 86656441, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of cis-(+/−)-5-(tert-butoxycarbonylamino)piperidine-3-carboxylic acid (1.0 eq.) in dichloromethane (0.2 M) was added DIEA (1.1 eq.), followed by N-(benzyloxycarbonyloxy)succinimide (1.0 eq.); the reaction was stirred at r.t. overnight. The solvent was removed under reduced pressure. To the crude was added EtOAc and 1N HCl. After extraction, the organic layer was washed with brine, dried and filtered, and concentrated to yield cis-(+/−)-1-(benzyloxycarbonyl)-5-(tert-butoxycarbonylamino)piperidine-3-carboxylic acid (99% yield) LCMS (m/z): 379.2 (MH+); LC Rt=3.55 min.

Workup

  1. customThe solvent was removed under reduced pressure
  2. additionTo the crude was added EtOAc and 1N HCl
  3. extractionAfter extraction
  4. washthe organic layer was washed with brine
  5. customdried
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-48002924cb2a4f9fab865d979b221acd
Source dataset
uspto-grants-2014_09
Patent number
US08822497B2

Reaction notes

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