Hydrochloric Acid → HCID 131715498, compound

HRID 649093Notes

Reaction equation

HRID 649093 reaction equation
Cl.[NH2:2][C@H:3]([C:5]([NH:7][C@H:8]([C:12]([NH:14][C@H:15]([C:31]([NH2:33])=[O:32])[CH2:16][CH2:17][CH2:18][CH2:19][NH:20][C:21]([O:23][CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)=[O:22])=[O:13])[CH:9]([CH3:11])[CH3:10])=[O:6])[CH3:4].FC(C(O)=O)(F)F.[NH:41]([C:79]([O:81][C:82]([CH3:85])([CH3:84])[CH3:83])=[O:80])[C@H:42]([C:58]([NH:60][C@H:61]([C:67]([NH:69][C@H:70]([C:75](NN)=[O:76])[CH2:71][CH2:72][CH2:73][CH3:74])=[O:68])[CH2:62][CH2:63][C:64](=[O:66])[NH2:65])=[O:59])[CH2:43][CH2:44][CH2:45][CH2:46][NH:47][C:48]([O:50][CH2:51][C:52]1[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=1)=[O:49]>CN(C=O)C.O1CCOCC1.N(OC(C)(C)C)=O.C(N(CC)CC)C>[NH:41]([C:79]([O:81][C:82]([CH3:83])([CH3:85])[CH3:84])=[O:80])[C@H:42]([C:58]([NH:60][C@H:61]([C:67]([NH:69][C@H:70]([C:75]([NH:2][C@H:3]([C:5]([NH:7][C@H:8]([C:12]([NH:14][C@H:15]([C:31]([NH2:33])=[O:32])[CH2:16][CH2:17][CH2:18][CH2:19][NH:20][C:21]([O:23][CH2:24][C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1)=[O:22])=[O:13])[CH:9]([CH3:11])[CH3:10])=[O:6])[CH3:4])=[O:76])[CH2:71][CH2:72][CH2:73][CH3:74])=[O:68])[CH2:62][CH2:63][C:64](=[O:66])[NH2:65])=[O:59])[CH2:43][CH2:44][CH2:45][CH2:46][NH:47][C:48]([O:50][CH2:51][C:52]1[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=1)=[O:49]

Participants

8

Reactant 3

HCID 313Hydrochloric Acid2×HCID 131715490HCID 131715490, compoundHCID 131715497BOC-Lys(CBZ)-Gln-Nle-NHNH2

Product 1

HCID 131715498HCID 131715498, compound

Reagents, catalysts & solvents 4

HCID 6228DimethylformamideSolvent2×HCID 8471TriethylamineSolvent3×HCID 10906Tert-Butyl nitriteSolvent2×HCID 312751,4-DioxaneSolvent2×

Conditions

Temperature
-30 °C

Procedure

0.58 g, 0.9 mmol) was dissolved in anhydrous DMF (18 ml) and cooled to -30° C. 4.56M HCl in dioxane (0.90 ml) was added followed by t-butyl nitrite (0.12 ml). The reaction was left for 30 to 40 min at -30° C. then cooled to -60° C. Triethylamine (0.60 ml) was added followed by the deprotected amide (X) (0.384 g, 0.68 mmol) and a further addition of triethylamine (0.1 ml). The mixture (M) was left to stand, reaching ambient temperature over 2 days. A further amount of (XIV) (0.29 g, 0.45 mmol) in DMF (10 ml) was treated at -30° C. with 4.5M HCl in dioxane (0.45 ml), t-butyl nitrite (0.06 ml) and triethylamine (0.3 ml) as described above and added to the reaction mixture (M) at -30° C. The whole was left to stand, reaching ambient temperature over a further 4 days.

Workup

  1. temperaturethen cooled to -60° C
  2. waitreaching ambient temperature over 2 days
  3. waitThe whole was left
  4. waitreaching ambient temperature over a further 4 days

Sources & evidence

ORD record
ord-7c519044335345df8ea1503807d8f89f
Source dataset
uspto-grants-1988_04
Patent number
US04737487

Reaction notes

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