Triethylamine → HCID 27866014, compound

HRID 384848Notes

Reaction equation

HRID 384848 reaction equation
Cl.[CH2:2](N=C=NCCCN(C)C)C.Cl.[CH2:14]([O:21][C:22]1[CH:29]=[CH:28][C:25]([CH2:26][NH2:27])=[CH:24][C:23]=1[O:30][CH3:31])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.[C:32]([O:36][C:37]([N:39]1[CH2:43][CH2:42][C@H:41]([C:44]([OH:46])=O)[CH2:40]1)=[O:38])([CH3:35])([CH3:34])[CH3:33].C(N(CC)CC)C>C(Cl)Cl>[CH2:14]([O:21][C:22]1[CH:29]=[CH:28][C:25]([CH2:26][NH:27][C:44]([C@H:41]2[CH2:2][CH2:42][CH2:43][N:39]([C:37]([O:36][C:32]([CH3:33])([CH3:34])[CH3:35])=[O:38])[CH2:40]2)=[O:46])=[CH:24][C:23]=1[O:30][CH3:31])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 1512492(3S)-1-[(tert-butoxy)carbonyl]pyrrolidine-3-carboxylic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 162477591-[4-(Benzyloxy)-3-methoxyphenyl]methanamine--hydrogen chloride (1/1)

Product 1

HCID 27866014HCID 27866014, compoundYield 69.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1-Ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (1.12 g) was added to a mixture of 4-benzyloxy-3-methoxybenzylamine hydrochloride (1.26 g), (S)-1-(t-butoxycarbonyl)pyrrolidine-3-carboxylic acid (0.97 g), triethylamine (0.82 ml) and methylene chloride (20 ml). After stirring the reaction mixture at room temperature for 20 hours, the mixture was washed with saturated ammonium chloride aqueous solution and then saturated brine, the organic layer was dried over sodium sulfate and the solvent was evaporated under reduced pressure. The residue was purified by silica gel chromatography (elution solvent: hexane/ethyl acetate=100/0 to 0/100 gradient) to obtain 1.42 g of t-butyl (S)-3-(4-benzyloxy-3-methoxybenzylcarbamoyl)-piperidine-1-carboxylate.

Workup

  1. washthe mixture was washed with saturated ammonium chloride aqueous solution
  2. dry with materialsaturated brine, the organic layer was dried over sodium sulfate
  3. customthe solvent was evaporated under reduced pressure
  4. customThe residue was purified by silica gel chromatography (elution solvent: hexane/ethyl acetate=100/0 to 0/100 gradient)

Sources & evidence

ORD record
ord-d3a4482c5e4647ba810198af6a42f1b1
Source dataset
uspto-grants-2013_02
Patent number
US08367835B2

Reaction notes

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