Triethylamine → HCID 69585605, compound

HRID 2188038Notes

Reaction equation

HRID 2188038 reaction equation
[C:1]([O:5][C:6]([C:8]1[C:16]2[CH2:15][C@@H:14]([C:17](O)=[O:18])[N:13]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:12][C:11]=2[S:10][C:9]=1[NH2:27])=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.ClC(OCC(C)C)=O.Cl.[NH2:44][C@H:45]([C:49]([OH:51])=O)[CH2:46][CH2:47][SH:48]>O1CCCC1>[C:1]([O:5][C:6]([C:8]1[C:16]2[CH2:15][C@@H:14]([C:17](=[O:18])[NH:44][CH:45]3[CH2:46][CH2:47][S:48][C:49]3=[O:51])[N:13]([C:20]([O:22][C:23]([CH3:25])([CH3:26])[CH3:24])=[O:21])[CH2:12][C:11]=2[S:10][C:9]=1[NH2:27])=[O:7])([CH3:2])([CH3:4])[CH3:3]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 62365Isobutyl chloroformateHCID 69585611HCID 69585611, compoundHCID 71587034Homocysteine hydrochloride

Product 1

HCID 69585605HCID 69585605, compoundYield 56.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2-amino-4,7-dihydro-5H-thieno[2,3-c]pyridine-3,5-(S),6-tri-carboxylic acid 3,6-di-tert-butyl ester (0.30 g, 0.75 mmol) and triethylamine (0.21 mL, 1.51 mmol) in tetrahydrofuran (10 mL) was cooled to −20° C. before isobutyl chloroformate (103 μL, 0.75 mmol) was added. The reaction mixture was stirred 15 min at −20° C. before homocystein hydrochloride (116 mg, 0.75 mmol) was added. The cooling bath was removed and the reaction mixture was left for 16 hours at room temperature. The solvent was removed in vacuo and the residue was subjected to column chromatography (SiO2, Flash 40, heptane/ethyl acetate 2:1) to give 212 mg (56%) of 2-amino-5-(S)-(2-oxo-tetrahydro-thiophen-3-ylcarbamoyl)-4,7-dihydro-5H-thieno[2,3-c]pyridine-3,6-dicarboxylic acid di-tert-butyl ester

Workup

  1. additionwas added
  2. additionwas added
  3. customThe cooling bath was removed
  4. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-e01a09d0ef6449d580343294dfb68fef
Source dataset
uspto-grants-2002_06
Patent number
US06410556B1

Reaction notes

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