HCID 131714616, compound → HCID 131714619, compound

HRID 236458Notes

Reaction equation

HRID 236458 reaction equation
N[C@H](C(CBr)=[O:8])CC(C)C.[NH:11]([C:44]([O:46][CH2:47][C:48]1[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=1)=[O:45])[C@H:12]([C:20]([NH:22][CH2:23][C:24]([NH:26][C@H:27]([C:32](N[C@H](C(CCl)=O)CC(C)C)=[O:33])[CH2:28]C(C)C)=[O:25])=[O:21])[CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>>[NH:11]([C:44]([O:46][CH2:47][C:48]1[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=1)=[O:45])[C@H:12]([C:20]([NH:22][CH2:23][C:24]([NH:26][C@H:27]([C:32]([OH:8])=[O:33])[CH3:28])=[O:25])=[O:21])[CH2:13][C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

3

Reactant 2

HCID 131714616HCID 131714616, compoundHCID 131715021HCID 131715021, compound

Product 1

HCID 131714619HCID 131714619, compound

Procedure

A mixed anhydride of Z-Phe-Gly-Ala-OH (0.41 g, 0.95 mmol) was prepared and coupled to H-LeuCH2Br.HBR substantially according to the procedure described for preparation of Z-Phe-Gly-Leu-LeuCH2Cl, above. The resulting product was crystallized from ethyl acetate:hexane to yield 0.30 g. Product was recrystallized from the same solvents to yield 0.07 g, m.p. 135.5°-138° (dec.).

Workup

  1. customThe resulting product was crystallized from ethyl acetate
  2. customhexane to yield 0.30 g
  3. customProduct was recrystallized from the same solvents
  4. customto yield 0.07 g, m.p. 135.5°-138° (dec.)

Sources & evidence

ORD record
ord-a9048eba781f4dcf867f02b532ccf81b
Source dataset
uspto-grants-1987_02
Patent number
US04644055

Reaction notes

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