4-Methylmorpholine → Boc-Tyr-(D)Ala-Gly-Phe methioninol

HRID 443920Notes

Reaction equation

HRID 443920 reaction equation
[NH:1]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[C@H:2]([C:11]([NH:13][C@@H:14]([C:16]([NH:18][CH2:19][C:20](O)=[O:21])=[O:17])[CH3:15])=[O:12])[CH2:3][C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1.CN1CCOCC1.C(OC(Cl)=O)C.[NH2:43][C@H:44]([C:52]([OH:54])=[O:53])[CH2:45][C:46]1[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=1.FC(F)(F)C(O)=O.[NH2:62][C@H:63]([CH2:68][OH:69])[CH2:64][CH2:65][S:66][CH3:67]>O1CCCC1.CN(C=O)C>[NH:1]([C:23]([O:25][C:26]([CH3:27])([CH3:29])[CH3:28])=[O:24])[C@H:2]([C:11]([NH:13][C@@H:14]([C:16]([NH:18][CH2:19][C:20]([NH:43][C@H:44]([C:52]([OH:54])=[O:53])[CH2:45][C:46]1[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=1)=[O:21])=[O:17])[CH3:15])=[O:12])[CH2:3][C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1.[NH2:62][C@H:63]([CH2:68][OH:69])[CH2:64][CH2:65][S:66][CH3:67]

Participants

7

Reactant 4

HCID 79724-Methylmorpholine2×HCID 10928Ethyl chloroformateHCID 7272028Boc-tyr-D-ala-gly-OHHCID 131712175H-Phe methioninol trifluoroacetate

Product 1

HCID 131712172Boc-Tyr-(D)Ala-Gly-Phe methioninol

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

4.1 g of Boc-Tyr-(D)Ala-Gly-OH and 1.1 ml of N-methyl-morpholine are dissolved in 50 ml of absolute tetrahydrofuran and 1.0 ml of chloroformic acid ethyl ester added dropwise at -15°. After 5 minutes, a solution of 4.0 g of H-Phe-methioninol trifluoroacetate and 1.2 ml of N-methylmorpholine in 50 ml of DMF is added. After 1 hour's stirring at 0°, the reaction mixture is evaporated and the residue taken up in acetic acid. The solution is repeatedly washed with 10% phosphoric acid and 1 N sodium bicarbonate. After evaporation of the acetic esters, the residue is crystallised from methanol/ether. M.P. 158°.

Workup

  1. customthe reaction mixture is evaporated
  2. washThe solution is repeatedly washed with 10% phosphoric acid and 1 N sodium bicarbonate
  3. customAfter evaporation of the acetic esters
  4. customthe residue is crystallised from methanol/ether

Sources & evidence

ORD record
ord-b8f3daf14e334c958628ebe0f1daf6f1
Source dataset
uspto-grants-1981_04
Patent number
US04261888

Reaction notes

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