4-Methylmorpholine → HCID 12083073, compound

HRID 1169008Notes

Reaction equation

HRID 1169008 reaction equation
C1C=CC2N(O)N=NC=2C=1.[NH:11]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[C@H:12]([C:22]([OH:24])=O)[CH2:13][S:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.[NH2:32][C@@H:33]([C:40]([O:42][CH2:43][CH3:44])=[O:41])[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1.Cl.CN1CCOCC1.CCN=C=NCCCN(C)C>O.CN(C=O)C>[NH:11]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[C@H:12]([C:22]([NH:32][C@@H:33]([C:40]([O:42][CH2:43][CH3:44])=[O:41])[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)=[O:24])[CH2:13][S:14][CH2:15][C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

Participants

8

Reactant 5

HCID 79724-MethylmorpholineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 2724757L-Cysteine, N-[(1,1-dimethylethoxy)carbonyl]-S-(phenylmethyl)-HCID 2083376517609-48-2

Product 1

HCID 12083073HCID 12083073, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

HOBt (1.90 g) was added to a DMF solution (50 ml) of Boc-Cys(Bzl)-OH (4.34 g) and D-Phg-OEt hydrochloride (3.00 g), to which were added N-methylmorpholine (1.65 ml) and WSC (4.00 g) at 0° C. The reaction mixture was stirred at 0° C. for 20 minutes and was further stirred at room temperature for 80 minutes, to which water was added, and extracted with AcOEt. The organic phase was washed with saturated saline, dried with magnesium sulfate anhydride, and then filtered and concentrated. The residue was purified by silica gel chromatography (h-hexane/AcOEt=4/1→2/1) to obtain Boc-Cys(Bzl)-D-Phg-OEt.

Workup

  1. additionwas added
  2. extractionextracted with AcOEt
  3. washThe organic phase was washed with saturated saline
  4. dry with materialdried with magnesium sulfate anhydride
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by silica gel chromatography (h-hexane/AcOEt=4/1→2/1)

Sources & evidence

ORD record
ord-f1d50d9be6f945aa8e07444689b6505c
Source dataset
uspto-grants-2003_09
Patent number
US06627732B1

Reaction notes

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