4-Methylmorpholine → HCID 57033220, compound

HRID 2258494Notes

Reaction equation

HRID 2258494 reaction equation
[S:1]1[CH2:5][CH:4]([C:6]([O-:8])=O)[N:3]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:2]1.CN1CC[O:20][CH2:19]C1.Cl.CO[N:26]([CH3:34])[C:27]([CH:29]1[CH2:33][S:32][CH2:31][NH:30]1)=[O:28].CCN=C=NCCCN(C)C.Cl>CN(C1C=CN=CC=1)C.C(Cl)Cl>[CH3:19][O:20][CH2:34][NH:26][C:27]([CH:29]1[CH2:33][S:32][CH2:31][N:30]1[C:6]([CH:4]1[CH2:5][S:1][CH2:2][N:3]1[C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])=[O:8])=[O:28]

Participants

7

Reactant 4

HCID 79724-MethylmorpholineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 23091968HCID 23091968, compoundHCID 131720135HCID 131720135, compound

Product 1

HCID 57033220HCID 57033220, compoundYield 25.6%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

To a stirred solution of 3,4-thiazolidinedicarboxylic acid, 3-(1,1-dimethylethyl) ester (compound from Example IIIA; 0.81 g, 3.49 mmol) and DMAP (0.43 g, 3.49 mmol) in methylene chloride (20 ml) under argon was added NMM (0.38 ml, 3.49 mmol) followed by N-methoxy-N-methyl-4-thiazolidinecarboxamide, monohydrochloride (compound from Example IIIC; 0.76 g, 3.49 mmol) in methylene chloride (10 ml) and water soluble carbodiimide (0.67 g; 3.49 mmol). After the reaction was complete the reaction was concentrated to about 10 ml and loaded onto a 5×13 cm silica gel column and subjected to flash chromatography, eluting with acetone/ethyl acetate (8:92). Product containing fractions were combined (Rf=0.66) and concentrated to give a white foam (0.35 g). Mass spectral analysis of the product gave MH+=392.1324 [expected mass for C15H60N3O5S2 (MH+)=392.1314].

Workup

  1. concentrationwas concentrated to about 10 ml
  2. washeluting with acetone/ethyl acetate (8:92)
  3. additionProduct containing fractions
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-fa8bf4b030c84223a34b1623637c74fa
Source dataset
uspto-grants-1997_08
Patent number
US05661167

Reaction notes

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