4-Methylmorpholine → methyl Boc-L-tyrosyl-D-methionyl-glycyl-L-phenylalanyl-3-amino-1-adamantanecarboxylate

HRID 1680567Notes

Reaction equation

HRID 1680567 reaction equation
Cl.[NH2:2][C@@H:3]([C:8]([NH:10][CH2:11][C:12]([NH:14][C@H:15]([C:23]([CH:25]1[C:32]2([NH2:34])[CH2:33][CH:28]3[CH2:29][CH:30]([CH2:35][C:26]1([C:36]([O:38][CH3:39])=[O:37])[CH2:27]3)[CH2:31]2)=[O:24])[CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:13])=[O:9])[CH2:4][CH2:5][S:6][CH3:7].ClC1C([O:47][C:48](=O)[C@H:49]([CH2:58][C:59]2[CH:64]=[CH:63][C:62]([OH:65])=[CH:61][CH:60]=2)[NH:50][C:51]([O:53][C:54]([CH3:57])([CH3:56])[CH3:55])=[O:52])=C(Cl)C(Cl)=C(Cl)C=1Cl.CN1CCOCC1>O1CCCC1.C(OCC)(=O)C>[C:51]([NH:50][C@H:49]([C:48]([NH:2][C@@H:3]([C:8]([NH:10][CH2:11][C:12]([NH:14][C@H:15]([C:23]([CH:25]1[C:32]2([NH2:34])[CH2:33][CH:28]3[CH2:29][CH:30]([CH2:35][C:26]1([C:36]([O:38][CH3:39])=[O:37])[CH2:27]3)[CH2:31]2)=[O:24])[CH2:16][C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1)=[O:13])=[O:9])[CH2:4][CH2:5][S:6][CH3:7])=[O:47])[CH2:58][C:59]1[CH:64]=[CH:63][C:62]([OH:65])=[CH:61][CH:60]=1)([O:53][C:54]([CH3:56])([CH3:55])[CH3:57])=[O:52]

Participants

6

Reactant 3

HCID 79724-MethylmorpholineHCID 15608388Boc-L-tyrosine pentachlorophenyl esterHCID 70568410methyl D-methionylglycyl-L-phenylalanyl-3-amino-1-adamantanecarboxylate hydrochloride

Product 1

HCID 70566106methyl Boc-L-tyrosyl-D-methionyl-glycyl-L-phenylalanyl-3-amino-1-adamantanecarboxylate

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 3.513 g of methyl D-methionylglycyl-L-phenylalanyl-3-amino-1-adamantanecarboxylate hydrochloride in 30 ml of tetrahydrofuran is added 3.17 g of Boc-L-tyrosine pentachlorophenyl ester followed by 1.12 ml of N-methylmorpholine. The reaction mixture is allowed to stand for 4 hours at room temperature then diluted with 200 ml ethyl acetate. The ethyl acetate layer is separated and washed three times with a 0.5 M solution of potassium bisulfate then dried over magnesium sulfate. The solvent is removed under reduced pressure and the residue is purified by low pressure chromatography on silica gel to give methyl Boc-L-tyrosyl-D-methionyl-glycyl-L-phenylalanyl-3-amino-1-adamantanecarboxylate which is represented by the following formula ##STR19##

Workup

  1. customThe ethyl acetate layer is separated
  2. washwashed three times with a 0.5 M solution of potassium bisulfate
  3. dry with materialthen dried over magnesium sulfate
  4. customThe solvent is removed under reduced pressure
  5. customthe residue is purified by low pressure chromatography on silica gel

Sources & evidence

ORD record
ord-c672792055b44548a85d22f9c9759c97
Source dataset
uspto-grants-1981_06
Patent number
US04273704

Reaction notes

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