4-Methylmorpholine → BOC-Cys(MBzl)-Thr-ol

HRID 1903334Notes

Reaction equation

HRID 1903334 reaction equation
CN1CCOCC1.[NH:8]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[C@H:9]([C:20]([OH:22])=O)[CH2:10][S:11][CH2:12][C:13]1[CH:19]=[CH:18][C:16]([CH3:17])=[CH:15][CH:14]=1.C(OC(Cl)=O)C(C)C.[NH2:38][C@H:39]([CH2:43][OH:44])[C@@H:40]([CH3:42])[OH:41].Cl>C1COCC1.CN(C=O)C>[NH:8]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[C@H:9]([C:20]([NH:38][C@H:39]([CH2:43][OH:44])[C@@H:40]([CH3:42])[OH:41])=[O:22])[CH2:10][S:11][CH2:12][C:13]1[CH:14]=[CH:15][C:16]([CH3:17])=[CH:18][CH:19]=1

Participants

7

Reactant 4

HCID 79724-Methylmorpholine2×HCID 62365Isobutyl chloroformateHCID 7010551N-alpha-t-Butyloxycarbonyl-S-(4-methyl-benzyl)-L-cysteineHCID 122236265(2R,3R)-2-aminobutane-1,3-diol hydrochloride

Product 1

HCID 131713414BOC-Cys(MBzl)-Thr-ol

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-10 °C

Procedure

2.1 ml N-methylmorpholine are added with stirring to a solution of 6.3 g Boc-Cys(MBzl)-OH in 50 ml THF, followed by drop-wise addition at -15° C. of 2.4 ml chloroformic acid isobutyl ester. After stirring for 5 minutes at -15° C. a solution of 3.3 g H-Thr-ol hydrochloride and 4.1 ml N-methylmorpholine in 30 ml DMF, pre-cooled to -10° C. is added. The reaction mixture is stirred for 2 hrs. at 0° C. and for a further 2 hrs. at room-temperature. 50 ml 10% KHCO3 -solution are added and the whole concentrated under vacuum. After dilution with AcOEt, washing 3× with 2 N citric acid, 3× with KHCO3 -solution and 1× with NaCl solution, the organic phase is dried over Na2SO4 and evaporated under vacuum to yield the title compound:

Workup

  1. additionis added
  2. waitat 0° C. and for a further 2 hrs
  3. concentrationthe whole concentrated under vacuum
  4. washAfter dilution with AcOEt, washing 3× with 2 N citric acid, 3× with KHCO3 -solution and 1× with NaCl solution
  5. dry with materialthe organic phase is dried over Na2SO4
  6. customevaporated under vacuum

Sources & evidence

ORD record
ord-7e91228172af46a2830e18e4f7934b6f
Source dataset
uspto-grants-1984_03
Patent number
US04435385

Reaction notes

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