4-Methylmorpholine → HCID 86604049, compound

HRID 2222965Notes

Reaction equation

HRID 2222965 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]([C:13]1[CH:18]=[CH:17][C:16]([O:19][CH2:20][CH2:21][O:22][CH3:23])=[CH:15][CH:14]=1)[C:10]([OH:12])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].ClC1N=C(OC)N=C(OC)N=1.CN1CCOCC1.[CH3:42][O:43][C:44]([C:46]1[N:47]=[C:48]([NH:51][C:52](=[O:62])[C@@H:53]([NH2:61])[CH2:54][C:55]2[CH:60]=[CH:59][CH:58]=[CH:57][CH:56]=2)[S:49][CH:50]=1)=[O:45]>O1CCCC1>[CH3:42][O:43][C:44]([C:46]1[N:47]=[C:48]([NH:51][C:52](=[O:62])[C@@H:53]([NH:61][C:10](=[O:12])[CH:9]([NH:8][C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])[C:13]2[CH:18]=[CH:17][C:16]([O:19][CH2:20][CH2:21][O:22][CH3:23])=[CH:15][CH:14]=2)[CH2:54][C:55]2[CH:60]=[CH:59][CH:58]=[CH:57][CH:56]=2)[S:49][CH:50]=1)=[O:45]

Participants

6

Reactant 4

HCID 79724-MethylmorpholineHCID 184502-Chloro-4,6-dimethoxy-1,3,5-triazineHCID 66815175(R)-tert-Butoxycarbonylamino-[4-(2-methoxy-ethoxy)-phenyl]-acetic acidHCID 866040402-((S)-2-amino-3-phenyl-propionylamino)-thiazole-4-carboxylic acid methyl ester

Product 1

HCID 86604049HCID 86604049, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

(R)-tert-butoxycarbonylamino-{4-[2-(methoxy)-ethoxy]-phenyl}-acetic acid (0.6 g, 1.84 mmol), 2-chloro-4,6-dimethoxy-1,3,5-triazine (0.32 g, 1.84 mmol) and N-methylmorpholine (0.19 g, 1.84 mmol) in anhydrous tetrahydrofuran (20 mL) were stirred at room temperature for 4 hours. Then a solution of 2-((S)-2-amino-3-phenyl-propionylamino)-thiazole-4-carboxylic acid methyl ester (0.56 g, 1.84 mmol) in tetrahydrofuran (10 mL) was added. The reaction mixture was stirred at room temperature for 20 hours. The mixture was filtered though a short pad of silica gel and the residual material eluted from the silica gel with ethyl acetate. The filtrate was concentrated. The residue was purified by chromatography over silica gel eluted with 1:1 ethyl acetate/hexanes to give 2-((S)-2-{2-tert-butoxycarbonylamino-2-[4-(2-methoxy-ethoxy)-phenyl]-acetylamino}-3-phenyl-propionylamino)-thiazole-4-carboxylic acid methyl ester as a mixture of two epimers (R/S=85:15) (0.21 g,

Workup

  1. filtrationThe mixture was filtered though a short pad of silica gel
  2. washthe residual material eluted from the silica gel with ethyl acetate
  3. concentrationThe filtrate was concentrated
  4. customThe residue was purified by chromatography over silica gel
  5. washeluted with 1:1 ethyl acetate/hexanes

Sources & evidence

ORD record
ord-cd5f15cfcffa47ccbf4a968c64a1cab3
Source dataset
uspto-grants-2008_05
Patent number
US07371869B2

Reaction notes

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