Hydrazine → HCID 131711182, compound

HRID 2419480Notes

Reaction equation

HRID 2419480 reaction equation
[NH:1]([C:48]([O:50][CH2:51][C:52]1[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=1)=[O:49])[C@H:2]([C:11]([NH:13][CH2:14][C:15]([NH:17][CH2:18][C:19]([NH:21][C@H:22]([C:30]([NH:32][C@H:33]([C:38](OCC1C=CC=CC=1)=[O:39])[CH2:34][CH2:35][S:36][CH3:37])=[O:31])[CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)=[O:20])=[O:16])=[O:12])[CH2:3][C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1.[NH2:58][NH2:59]>CN(C=O)C>[NH:1]([C:48]([O:50][CH2:51][C:52]1[CH:53]=[CH:54][CH:55]=[CH:56][CH:57]=1)=[O:49])[C@H:2]([C:11]([NH:13][CH2:14][C:15]([NH:17][CH2:18][C:19]([NH:21][C@H:22]([C:30]([NH:32][C@H:33]([C:38]([NH:58][NH2:59])=[O:39])[CH2:34][CH2:35][S:36][CH3:37])=[O:31])[CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)=[O:20])=[O:16])=[O:12])[CH2:3][C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1

Participants

4

Reactant 2

HCID 9321HydrazineHCID 131711183HCID 131711183, compound

Product 1

HCID 131711182HCID 131711182, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

Compound I, Z-Tyr-Gly-Gly-Phe-Met-OBzl (0.85 g, 1.07 mmol) was dissolved in DMF (10 ml, purged with Argon for 15 min) and treated with 0.34 ml of H2NNH2 for 72 hr. at 25° C. The solvent was removed under reduced pressure to yield a crystalline residue which was triturated with H2O to form a crystalline product, yield 0.65g (84.2%). Recrystallized from DMF and ethanol to give colorless needles; mp 209°-213° C.; [α]D25 -27.6° (c 1, DMF). Anal. Calcd for C35H43N7O8S1 (721.84): C, 58.24; H, 6.00; N, 13.58; S, 4.44. Found: C, 57.50; H, 6.04; N, 13.75; S, 4.67.

Workup

  1. customat 25° C
  2. customThe solvent was removed under reduced pressure
  3. customto yield a crystalline residue which
  4. customwas triturated with H2O
  5. customto form a crystalline product, yield 0.65g (84.2%)
  6. customRecrystallized from DMF and ethanol
  7. customto give colorless needles

Sources & evidence

ORD record
ord-2789612f3a9d4539a8d0cf646a185c43
Source dataset
uspto-grants-1978_08
Patent number
US04105652

Reaction notes

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