(3S)-2-((tert-butoxy)carbonyl)-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid → HCID 131727458, compound

HRID 1983565Notes

Reaction equation

HRID 1983565 reaction equation
[C:1]([O:5][C:6]([N:8]1[C@H:17]([C:18](O)=[O:19])[CH2:16][C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[NH2:21][C:22]1[CH:23]=[N:24][C:25]([CH2:28][CH2:29][CH2:30][CH2:31][CH3:32])=[CH:26][CH:27]=1.Cl.CN(C)CCCN=C=NCC>C(Cl)(Cl)Cl.CN(C)C1C=CN=CC=1>[CH2:28]([C:25]1[N:24]=[CH:23][C:22]([NH:21][C:18]([C@@H:17]2[CH2:16][C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[CH2:9][N:8]2[C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:7])=[O:19])=[CH:27][CH:26]=1)[CH2:29][CH2:30][CH2:31][CH3:32]

Participants

6

Reactant 3

HCID 664088(3S)-2-((tert-butoxy)carbonyl)-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 13860731HCID 13860731, compound

Product 1

HCID 131727458HCID 131727458, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6212ChloroformSolvent

Procedure

To a stirred solution of (S)—N-(tert-butoxycarbonyl)-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid (0.666 g, 2.40 mmol) and 3-amino-6-pentylpyridine (0.330 g, 2.01 mmol) in chloroform (10 mL) was added 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride (0.460 g, 2.40 mmol) and a catalytic amount of 4-(dimethylamino)pyridine. The reaction was allowed to proceed overnight and then partitioned between methylene chloride and aqueous sodium bicarbonate solution. The organic layer was dried (sodium sulfate) and concentrated to afford a faint green foam.

Workup

  1. custompartitioned between methylene chloride and aqueous sodium bicarbonate solution
  2. dry with materialThe organic layer was dried (sodium sulfate)
  3. concentrationconcentrated
  4. customto afford a faint green foam

Sources & evidence

ORD record
ord-76aa27f653564e2ab10a983ca573daba
Source dataset
uspto-grants-2009_06
Patent number
US07541466B2

Reaction notes

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