Hydrochloric Acid → HCID 131712845, compound

HRID 1703037Notes

Reaction equation

HRID 1703037 reaction equation
[NH:1]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[C@H:2]([C:11]([OH:13])=[O:12])[CH2:3][C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1.[CH3:21][C@H:22]([NH2:37])[C:23]([NH:25][C@H:26]([C:34]([OH:36])=[O:35])[CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)=[O:24].[NH2:38][CH2:39][C:40](NN)=[O:41].Cl.N(OCCCC)=O.CN1CCOCC1.[NH2:59][C@H:60]([C:69]([NH2:71])=[O:70])[CH2:61][C:62]1[CH:67]=[CH:66][C:65]([OH:68])=[CH:64][CH:63]=1.Cl>CN(C)C=O.O1CCCC1.CO>[NH:1]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[C@H:2]([C:11]([OH:13])=[O:12])[CH2:3][C:4]1[CH:5]=[CH:6][C:7]([OH:10])=[CH:8][CH:9]=1.[CH3:21][C@H:22]([NH2:37])[C:23]([NH:25][C@H:26]([C:34]([OH:36])=[O:35])[CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)=[O:24].[CH:67]1[C:62]([CH2:61][C@H:60]([NH:59][C:40]([CH2:39][NH2:38])=[O:41])[C:69]([NH2:71])=[O:70])=[CH:63][CH:64]=[C:65]([OH:68])[CH:66]=1

Participants

9

Reactant 5

HCID 313Hydrochloric AcidHCID 79724-Methylmorpholine2×HCID 10996Butyl nitriteHCID 45157672L-Tyrosinamide--hydrogen chloride (1/1)HCID 131712846HCID 131712846, compound

Product 1

HCID 131712845HCID 131712845, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 6228DimethylformamideSolvent2×HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-30 °C

Procedure

2.74 g (4.8 mmoles) Boc-Tyr-ala-Phe-Gly-NH-NH2 (10) are dissolved in 50 ml anhydrous dimethylformamide and cooled at -30° C. 2.0 ml (12 mmoles) 6 N hydrogen chloride in anhydrous tetrahydrofuran and 0.63 ml (5.28 mmoles) n-butyl nitrite are successively added and the reaction mixture is stirred for 30 min. at -30° C. 1.34 ml (12 mmoles) N-methyl-morpholine are added at -40° C., followed by a precooled (-40° C.) solution of 0.865 g (4.0 mmoles) H-Tyr-NH2.HCl (K. Blau and S. G. Waley, Biochem. J., 57, 538, 1954) and 0.456 ml (4.0 mmoles) N-methylmorpholine in 50 ml dimethylformamide. The reaction mixture is allowed to react for 7 days at -10° C., then it is concentrated to small volume, filtered from salt, and the product precipitated by dilution with chloroform. By crystallization from methyl alcohol-chloroform, 2.0 g of (14) are obtained, m.p. 127°-129° C.; [α]D25 +19.9° (C=1, MeOH); RfA =0.15, RfB =0.56.

Workup

  1. customto react for 7 days at -10° C.
  2. concentrationit is concentrated to small volume
  3. filtrationfiltered from salt
  4. customthe product precipitated by dilution with chloroform
  5. customBy crystallization from methyl alcohol-chloroform, 2.0 g of (14)
  6. customare obtained

Sources & evidence

ORD record
ord-e66e858b216442688e9f4667de3aeaec
Source dataset
uspto-grants-1982_09
Patent number
US04350627

Reaction notes

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