Hydrochloric Acid → HCID 131715641, compound

HRID 845672Notes

Reaction equation

HRID 845672 reaction equation
[NH:1]([C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])[C@H:2]([C:5]([NH:7][C@H:8]([C:13]([NH:15][C@H:16]([C:21]([NH:23][C@H:24]([C:27]([NH:29]N)=[O:28])[CH2:25][OH:26])=[O:22])[CH2:17][CH:18]([CH3:20])[CH3:19])=[O:14])[CH2:9][C:10](=[O:12])[NH2:11])=[O:6])[CH2:3][OH:4].Cl.C(ON=O)(C)(C)C.N[C@H:47]([C:51]([NH:53][C@H:54]([C:62]([NH:64][C@H:65]([C:69]([NH:71][C@H:72]([C:77]([OH:79])=[O:78])[CH2:73][CH:74]([CH3:76])[CH3:75])=[O:70])[CH:66]([CH3:68])[CH3:67])=[O:63])[CH2:55][S:56][CH2:57][NH:58][C:59]([CH3:61])=[O:60])=[O:52])[C@@H:48]([CH3:50])[OH:49]>CN(C)C=O.O1CCOCC1.C(N(CC)CC)C>[NH:1]([C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])[C@H:2]([C:5]([NH:7][C@H:8]([C:13]([NH:15][C@H:16]([C:21]([NH:23][C@H:24]([C:27]([NH:29][C@H:47]([C:51]([NH:53][C@H:54]([C:62]([NH:64][C@H:65]([C:69]([NH:71][C@H:72]([C:77]([OH:79])=[O:78])[CH2:73][CH:74]([CH3:76])[CH3:75])=[O:70])[CH:66]([CH3:68])[CH3:67])=[O:63])[CH2:55][S:56][CH2:57][NH:58][C:59]([CH3:61])=[O:60])=[O:52])[C@@H:48]([CH3:50])[OH:49])=[O:28])[CH2:25][OH:26])=[O:22])[CH2:17][CH:18]([CH3:20])[CH3:19])=[O:14])[CH2:9][C:10](=[O:12])[NH2:11])=[O:6])[CH2:3][OH:4]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 10906Tert-Butyl nitriteHCID 131715640HCID 131715640, compoundHCID 131715642HCID 131715642, compound

Product 1

HCID 131715641HCID 131715641, compound

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 8471TriethylamineSolventHCID 312751,4-DioxaneSolvent

Procedure

13.6 g of Boc-Ser-Asn-Leu-Ser-NHNH2 are dissolved in 150 ml of dimethylformamide, cooled to -20°, then 40 ml of an anhydrous solution of HCl (2N) in dioxane are added, followed by 3.6 ml of tert.-butylnitrite. After 10 minutes at -20°, 16 ml of triethylamine and 13.0 g of H-Thr-Cys(Acm)-Val-Leu-OH are added, and the solution stirred for 16 hours at 25°. The mixture is filtered, the filtrate is evaporated to dryness, the residue is suspended repeatedly in 1N acetic acid and in water, filtered and dried to give the title compound.

Workup

  1. temperaturecooled to -20°
  2. filtrationThe mixture is filtered
  3. customthe filtrate is evaporated to dryness
  4. filtrationfiltered
  5. customdried

Sources & evidence

ORD record
ord-9d442e81400942ae867e032d9362cbd1
Source dataset
uspto-grants-1988_07
Patent number
US04758550

Reaction notes

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