Glycine → HCID 11857332, compound

HRID 2258308

Reaction equation

HRID 2258308 reaction equation
[CH2:1]([N:3]1[CH2:8][CH2:7][O:6][CH2:5]C1)[CH3:2].ON1[C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=2N=N1.COS([C:24]1[CH:29]=[CH:28][C:27]([CH3:30])=[CH:26][CH:25]=1)(=O)=O.C1(N=C=NCCN2CC[O:45][CH2:44]C2)CCCCC1.[Cl:48]C1C=CN=C(C(O)=O)C=1OC.S([C:64]1[CH:70]=CC(C)=C[CH:65]=1)(O)(=O)=O.C(O[C:88](=[O:91])[CH2:89][NH2:90])CCCCCCCCCCCCCCC.NCC(O)=O.[CH2:97](O)CCCCCCCCCCCCCCC.C1(C)C=CC(S(O)(=O)=O)=CC=1.[OH2:125]>ClCCl.C1(C)C=CC=CC=1>[ClH:48].[CH2:65]([O:125][C:88]([CH2:89][NH:90][C:44]([C:8]1[C:7]([O:6][CH3:5])=[CH:97][CH:2]=[CH:1][N:3]=1)=[O:45])=[O:91])[CH2:64][CH2:70][CH2:26][CH2:25][CH2:24][CH2:29][CH2:28][CH2:27][CH2:30][CH2:13][CH2:18][CH2:17][CH2:16][CH2:15][CH3:14]

Participants

12

Reactant 9

HCID 750GlycineHCID 962WaterHCID 2682Cetyl AlcoholHCID 6101p-Toluenesulfonic acidHCID 7525EthylmorpholineHCID 757711-HydroxybenzotriazoleHCID 9954069N-cyclohexyl-N'-(2-morpholinoethyl)-carbodiimide methyl-p-toluenesulfonateHCID 22363159HCID 22363159, compoundHCID 229238434-Chloro-3-methoxypyridine-2-carboxylic acid

Product 1

HCID 11857332HCID 11857332, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6344DichloromethaneSolvent

Procedure

7.7 ml (60mmol) of N-ethylmorpholine, 4.5 g (33mmol) of 1-hydroxy-1H-benzotriazole and 12.8 g (30 mmol) of N-cyclohexyl-N'-(2-morpholinoethyl)-carbodiimide methyl-p-toluenesulfonate (CMC) were added, in analogy with Examples 90b) and c), to 5.7 g (30 mmol) of 4-chloro-3-methoxypyridine-2-carboxylic acid and 14.2 g (30mmol) of glycine hexadecyl ester tosylate (m.p. approximately 90° C., prepared from glycine, 1-hexadecanol and p-toluene-sulfonic acid on a water separator using toluene) in 300 ml of dichloromethane, and the mixture was stirred for 24 h. The undissolved material was then filtered off with suction and the filtrate was extracted by shaking with an aqueous solution of Na bicarbonate, with water and with aqueous hydrochloric acids the organic phase was concentrated and the residue (14 g) was dissolved in 500 ml of tetrahydrofuran/methanol (1:1), and after that Pd/C (10%) was added to this mixture, which was hydrogenated using a hydrogenation vessel. Once the uptake of hydrogen was complete, the catalyst was filtered off with suction and the filtrate was concentrated and the residue chromatographed on silica gel using ethyl acetate. Appropriate fractions were concentrated and the residue was crystallized using diisopropyl ether. 2.1 g of the title compound were obtained as a colorless substance, m.p. 63°-65° C.

Workup

  1. filtrationThe undissolved material was then filtered off with suction
  2. extractionthe filtrate was extracted
  3. stirringby shaking with an aqueous solution of Na bicarbonate, with water and with aqueous hydrochloric acids the organic phase
  4. concentrationwas concentrated
  5. dissolutionthe residue (14 g) was dissolved in 500 ml of tetrahydrofuran/methanol (1:1)
  6. additionafter that Pd/C (10%) was added to this mixture, which
  7. filtrationthe catalyst was filtered off with suction
  8. concentrationthe filtrate was concentrated
  9. customthe residue chromatographed on silica gel
  10. concentrationAppropriate fractions were concentrated
  11. customthe residue was crystallized

Sources & evidence

ORD record
ord-63be882210bc4aa79450fc678d22ca91
Source dataset
uspto-grants-1997_08
Patent number
US05658933

Linked notes

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