L-Tyrosine, N-(1,1-dimethylethoxy)carbonyl- → HCID 18351237, compound

HRID 636698Notes

Reaction equation

HRID 636698 reaction equation
[NH2:1][C:2]1[S:10][C:5]2[CH2:6][NH:7][CH2:8][CH2:9][C:4]=2[C:3]=1[C:11](=[O:18])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.[NH:19]([C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])[C@H:20]([C:29](O)=[O:30])[CH2:21][C:22]1[CH:27]=[CH:26][C:25]([OH:28])=[CH:24][CH:23]=1.CCN=C=NCCCN(C)C.Cl>CN(C=O)C.C(=O)(O)[O-].[Na+]>[NH2:1][C:2]1[S:10][C:5]2[CH2:6][N:7]([C:29](=[O:30])[CH:20]([NH:19][C:32]([O:34][C:35]([CH3:37])([CH3:36])[CH3:38])=[O:33])[CH2:21][C:22]3[CH:23]=[CH:24][C:25]([OH:28])=[CH:26][CH:27]=3)[CH2:8][CH2:9][C:4]=2[C:3]=1[C:11](=[O:18])[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

6

Reactant 3

HCID 117439L-Tyrosine, N-(1,1-dimethylethoxy)carbonyl-HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 15434454(2-Amino-4,5,6,7-tetrahydrothieno[2,3-c]pyridin-3-yl)phenylmethanone

Product 1

HCID 18351237HCID 18351237, compoundYield 84%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 516892Sodium BicarbonateSolvent

Procedure

To an ice-cooled and stirred solution of 2-amino-3-benzoyl4,5,6,7-tetrahydrothieno[2,3-c]pyridine (0.775 mmol) in dry DMF (11 mL), was added BOC-Tyr-OH (0.08 mmol) and EDCl (0.08, 0.445 g) under an argon atmosphere. After stirring overnight, the mixture was evaporated under vacuum to give a solid residue, which was dissolved in a saturated sodium bicarbonate solution and is extracted with ethyl acetate (3×20 mL), then dried on magnesium sulfate. The organic layers were evaporated under vacuum to give a solid which is chromatographed on silica gel column eluting with ethyl acetate and petroleum ether to afford 2-amino-3-benzoyl-6-[2-t-butoxycarbonylamino-3-(4-hydroxyphenyl)-propion-yl]-4,5,6,7-tetrahydrothieno[2,3-c]pyridine a yellow solid.

Workup

  1. customthe mixture was evaporated under vacuum
  2. customto give a solid residue, which
  3. extractionis extracted with ethyl acetate (3×20 mL)
  4. customdried on magnesium sulfate
  5. customThe organic layers were evaporated under vacuum
  6. customto give a solid which
  7. customis chromatographed on silica gel column
  8. washeluting with ethyl acetate and petroleum ether

Sources & evidence

ORD record
ord-ac98e1eca9be4c828714b3fc53190fa8
Source dataset
uspto-grants-2001_02
Patent number
US06194449B1

Reaction notes

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