Hydrochloric Acid → HCID 131712072, compound

HRID 1390155Notes

Reaction equation

HRID 1390155 reaction equation
[NH:1]([C:35]([O:37][C:38]([CH3:41])([CH3:40])[CH3:39])=[O:36])[C@H:2]([C:11]([NH:13][C@@H:14]([C:16]([NH:18][CH2:19][C:20]([NH:22][C@H:23]([C:31]([NH:33]N)=[O:32])[CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)=[O:21])=[O:17])[CH3:15])=[O:12])[CH2:3][C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1.Cl.C(N(CC)CC)C.N[C@H:51]([C:56]([OH:58])=[O:57])[CH2:52][CH2:53][S:54][CH3:55].[NH2:59][CH:60]([CH2:63][OH:64])[CH2:61][OH:62]>CN(C=O)C.O1CCOCC1.C(ON=O)(C)(C)C>[NH:1]([C:35]([O:37][C:38]([CH3:41])([CH3:40])[CH3:39])=[O:36])[C@H:2]([C:11]([NH:13][C@@H:14]([C:16]([NH:18][CH2:19][C:20]([NH:22][C@H:23]([C:31]([NH:33][C@H:51]([C:56]([OH:58])=[O:57])[CH2:52][CH2:53][S:54][CH3:55])=[O:32])[CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)=[O:21])=[O:17])[CH3:15])=[O:12])[CH2:3][C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1.[NH2:59][CH:60]([CH2:63][OH:64])[CH2:61][OH:62]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 15567271HCID 15567271, compoundHCID 131712074HCID 131712074, compound

Product 1

HCID 131712072HCID 131712072, compound

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 10906Tert-Butyl nitriteSolventHCID 312751,4-DioxaneSolvent

Procedure

To 2.5 g of Boc-Tyr-(D)-Ala-Gly-Phe-NHNH2 in 40 ml of DMF are added 2.7 ml of 5.6 N HCl in dioxane and 0.52 ml of tert.butylnitrite at -20° and, after 10 minutes, 3.4 ml of triethylamine and 2 g of H-Met-serinol trifuloroacetate. After 4 hours at 0° and 15 hours at room temperature, the mixture is concentrated under vacuum, the residue taken up in ethyl acetate and washed repeatedly with dilute HCl and water and the organic phase evaporated. The residue crystallizes from methanol/ether to yield the title compound. M.P. 140° (decomp.). [α]D20 =-15 (C=1 in DMF).

Workup

  1. waitAfter 4 hours at 0°
  2. concentration15 hours at room temperature, the mixture is concentrated under vacuum
  3. washwashed repeatedly with dilute HCl and water
  4. customthe organic phase evaporated
  5. customThe residue crystallizes from methanol/ether

Sources & evidence

ORD record
ord-b1900af5bb45498380345384c372f0b5
Source dataset
uspto-grants-1981_01
Patent number
US04247543

Reaction notes

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