Dichloromethane → HCID 67262978, compound

HRID 1755567Notes

Reaction equation

HRID 1755567 reaction equation
[OH:1][C:2]1[C:3]([CH3:18])=[C:4]2[C:9](=[C:10]([CH3:13])[C:11]=1[CH3:12])[O:8][C:7]([CH3:17])([C:14]([OH:16])=O)[CH2:6][CH2:5]2.C1N=CN(C(N2C=NC=C2)=O)C=1.Cl.[CH3:32][O:33][C:34](=[O:37])[CH2:35][NH2:36].C(Cl)Cl>C1COCC1.CO.CCN(CC)CC>[OH:1][C:2]1[C:3]([CH3:18])=[C:4]2[C:9](=[C:10]([CH3:13])[C:11]=1[CH3:12])[O:8][C:7]([CH3:17])([C:14]([NH:36][CH2:35][C:34]([O:33][CH3:32])=[O:37])=[O:16])[CH2:6][CH2:5]2

Participants

8

Reactant 4

HCID 6344DichloromethaneHCID 40634TroloxHCID 682631,1'-CarbonyldiimidazoleHCID 122755Glycine methyl ester hydrochloride

Product 1

HCID 67262978HCID 67262978, compoundYield 73.3%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent2×HCID 8471TriethylamineSolvent

Procedure

Following the amide coupling procedure described in protocol A, 499 mg 6-hydroxy-2,5,7,8-tetramethylchroman-2-carboxylic acid (2.00 mmol), and 361 mg CDI (2.23 mmol) were dissolved in THF. Glycine methyl ester hydrochloride (263.7 mg, 2.1 mmol) dissolved into 10 mL THF, 5 mL CH2Cl2, 100 μL, Et3N and 2.5 mL MeOH was added over 1 h. Workup as described in protocol A, produced 471.3 mg of methyl 2-(6-hydroxy-2,5,7,8-tetramethylchroman-2-carboxamido)acetate

Workup

  1. additionwas added over 1 h

Sources & evidence

ORD record
ord-67bbf7d3a39f4854a734990765e8e658
Source dataset
uspto-grants-2015_10
Patent number
US09169196B2

Reaction notes

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