Hydrochloric Acid → HCID 178455934, compound

HRID 365055Notes

Reaction equation

HRID 365055 reaction equation
[NH:1](C(OC(C)(C)C)=O)[C@H:2]([C:14]([NH:16][C@H:17]([C:28]([NH:30][C@H:31]([C:36]([NH:38][CH2:39][C:40]([O:42][CH3:43])=[O:41])=[O:37])[C@H:32]([CH2:34][CH3:35])[CH3:33])=[O:29])[CH2:18][CH2:19][CH2:20][NH:21][C:22](=[NH:27])[NH:23][N+:24]([O-:26])=[O:25])=[O:15])[CH2:3][C:4](=[O:13])[O:5][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.Cl>CCOC(C)=O>[NH2:1][C@H:2]([C:14]([NH:16][C@H:17]([C:28]([NH:30][C@H:31]([C:36]([NH:38][CH2:39][C:40]([O:42][CH3:43])=[O:41])=[O:37])[C@H:32]([CH2:34][CH3:35])[CH3:33])=[O:29])[CH2:18][CH2:19][CH2:20][NH:21][C:22](=[NH:27])[NH:23][N+:24]([O-:26])=[O:25])=[O:15])[CH2:3][C:4](=[O:13])[O:5][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 178455933HCID 178455933, compound

Product 1

HCID 178455934HCID 178455934, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A sample of the tetrapeptide (10) suspended in EtOAc is cooled to -40° under slow nitrogen flow, and is saturated with HCl gas, keeping the temperature from rising above -10°. Five min after saturation, the solution is purged with nitrogen for 60 min; addition of 80 mL of ether precipitates the title compound (11) as a white solid, which is collected by filtration, washed with ether, and dried in vacuo.

Workup

  1. temperatureis cooled to -40° under slow nitrogen flow
  2. customfrom rising above -10°
  3. customFive min after saturation, the solution is purged with nitrogen for 60 min
  4. additionaddition of 80 mL of ether
  5. customprecipitates the title compound (11) as a white solid, which
  6. filtrationis collected by filtration
  7. washwashed with ether
  8. customdried in vacuo

Sources & evidence

ORD record
ord-1a1ab6a227b548a592d9e7d9582357c5
Source dataset
uspto-grants-1986_08
Patent number
US04607023

Reaction notes

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