Glycine → HCID 9797241, compound

HRID 2258309Notes

Reaction equation

HRID 2258309 reaction equation
Cl.[CH3:2][O:3][C:4]1[C:5]([C:10]([OH:12])=O)=[N:6][CH:7]=[CH:8][CH:9]=1.C(N1CCOCC1)C.ON1C2C=CC=CC=2N=N1.S(C1C=CC(C)=CC=1)(O)(=O)=O.[CH2:42]([O:50][C:51](=[O:54])[CH2:52][NH2:53])[CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH3:49].NCC(O)=O>ClCCl.C1(C)C=CC=CC=1.O.C(O)CCCCCCC>[CH2:42]([O:50][C:51]([CH2:52][NH:53][C:10]([C:5]1[C:4]([O:3][CH3:2])=[CH:9][CH:8]=[CH:7][N:6]=1)=[O:12])=[O:54])[CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH3:49]

Participants

10

Reactant 5

HCID 750GlycineHCID 7525EthylmorpholineHCID 757711-HydroxybenzotriazoleHCID 19428418HCID 19428418, compoundHCID 67715990170622-23-8

Product 1

HCID 9797241HCID 9797241, compound

Reagents, catalysts & solvents 4

HCID 9571-OctanolSolventHCID 962WaterSolventHCID 1140TolueneSolventHCID 6344DichloromethaneSolvent

Procedure

2.5 g (13 mmol) of 3-methoxypyridine-2-carboxylic acid hydrochloride (m.p. 170° C. with decomp. (from ethyl acetate)), 5.5 ml (45 mmol) N-ethylmorpholine, 2 g (15 mmol) of 1-hydroxy-(1H)-benzotriazole, 4.7 g (13 mmol) of glycine octyl ester tosylate (prepared from glycine, octanol and p-Tos OH on a water separator using toluene) and 6.3 g (15 mmol) of CMC (cf. Example 146) were stirred for 48 h in 350 ml of anhydrous dichloromethane. Following a working up which was analogous to that in Example 146, the crude product was chromatographed on silica gel using dichloromethane (with the addition of up to 2.5% methanol during the course of this). 3.6 g were obtained of the colorless, oily title compound, 1H NMR (CDCl3): δ=4.26 (d, CH2 -glycine).

Workup

  1. customthe crude product was chromatographed on silica gel
  2. additionwith the addition of up to 2.5% methanol during the course of this)

Sources & evidence

ORD record
ord-ce04813598e849e68d25f913680e1407
Source dataset
uspto-grants-1997_08
Patent number
US05658933

Reaction notes

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