4-Methylmorpholine → HCID 22816339, compound

HRID 1680583Notes

Reaction equation

HRID 1680583 reaction equation
[C:1]([NH:8][C@H:9]([C:18]([NH:20][C@@H:21]([C:26]([NH:28][CH2:29][C:30](O)=[O:31])=[O:27])[CH2:22][CH2:23][S:24][CH3:25])=[O:19])[CH2:10][C:11]1[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][CH:12]=1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].CN1CCOCC1.C(OC(Cl)=O)C(C)C.[NH2:48][C@H:49]([C:57]([CH:59]1[CH:66]2[CH2:67][CH:62]3[CH2:63][CH:64]([CH2:68][C:60]1([NH2:69])[CH2:61]3)[CH2:65]2)=[O:58])[CH2:50][C:51]1[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=1>O1CCCC1>[C:1]([NH:8][C@H:9]([C:18]([NH:20][C@@H:21]([C:26]([NH:28][CH2:29][C:30]([NH:48][C@H:49]([C:57]([CH:59]1[CH:66]2[CH2:67][CH:62]3[CH2:63][CH:64]([CH2:68][C:60]1([NH2:69])[CH2:61]3)[CH2:65]2)=[O:58])[CH2:50][C:51]1[CH:52]=[CH:53][CH:54]=[CH:55][CH:56]=1)=[O:31])=[O:27])[CH2:22][CH2:23][S:24][CH3:25])=[O:19])[CH2:10][C:11]1[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][CH:12]=1)([O:3][C:4]([CH3:7])([CH3:5])[CH3:6])=[O:2]

Participants

6

Reactant 4

HCID 79724-MethylmorpholineHCID 62365Isobutyl chloroformateHCID 12919645N-(tert-Butoxycarbonyl)-L-tyrosyl-D-methionylglycineHCID 22816346HCID 22816346, compound

Product 1

HCID 22816339HCID 22816339, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-20 °C

Procedure

A solution of 1.88 g of Boc-L-tyrosyl-D-methionyl-glycine and 0.45 ml of N-methylmorpholine in 25 ml of dry tetrahydrofuran under nitrogen is cooled to -45° C. with stirring. To the cooled solution is added 0.52 ml of isobutylchloroformate. The reaction mixture is allowed to warm to -20° C. over a 10 minute period and is then cooled to -35° C. Following the addition of 1.9 g of L-phenylalanyl-1-aminoadamantane the reaction mixture is warmed to room temperature and allowed to stand overnight. The reaction mixture is filtered and the tetrahydrofuran is removed under reduced pressure. The residue is dissolved in methylene chloride and washed with cold 1 M potassium bisulfate solution and saturated sodium chloride solution. Removal of the solvent and purification by chromatography on silica gel gives Boc-tyrosyl-D-methionyl-glycyl-phenylalanyl-1-aminoadamantane which is represented by the following formula ##STR39##

Workup

  1. temperatureis then cooled to -35° C
  2. temperatureis warmed to room temperature
  3. filtrationThe reaction mixture is filtered
  4. customthe tetrahydrofuran is removed under reduced pressure
  5. dissolutionThe residue is dissolved in methylene chloride
  6. washwashed with cold 1 M potassium bisulfate solution and saturated sodium chloride solution
  7. customRemoval of the solvent and purification by chromatography on silica gel

Sources & evidence

ORD record
ord-bd67d4a4672740b08423ab8d8bc615e9
Source dataset
uspto-grants-1981_06
Patent number
US04273704

Reaction notes

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