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Hydrochloric Acid → HCID 131711714, compound

HRID 1448775
Notes
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Reaction equation

HRID 1448775 reaction equation
Cl.[NH:2]([C:33]([O:35][CH2:36][C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)=[O:34])[C@H:3]([C:14]([NH:16][C@H:17]([C:19]([NH:21][C@H:22]([C:25]([NH:27][CH2:28][C:29]([NH:31]N)=[O:30])=[O:26])[CH2:23][OH:24])=[O:20])[CH3:18])=[O:15])[CH2:4][C:5]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[NH:7][CH:6]=1.N[C@H:44]([CH2:49][OH:50])[CH2:45][C:46](=[O:48])[NH2:47].C(N(CC)CC)C>O1CCOCC1.N(OC(C)(C)C)=O.CN(C=O)C.C(OCC)(=O)C>[NH:2]([C:33]([O:35][CH2:36][C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)=[O:34])[C@H:3]([C:14]([NH:16][C@H:17]([C:19]([NH:21][C@H:22]([C:25]([NH:27][CH2:28][C:29]([NH:31][C@H:44]([CH2:49][OH:50])[CH2:45][C:46](=[O:48])[NH2:47])=[O:30])=[O:26])[CH2:23][OH:24])=[O:20])[CH3:18])=[O:15])[CH2:4][C:5]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[NH:7][CH:6]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

9

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 3082455AsparaginolHCID 131711715HCID 131711715, compound

Product 1

HCID 131711714HCID 131711714, compound

Reagents, catalysts & solvents 4

HCID 6228
Dimethylformamide
Solvent
HCID 8857Ethyl AcetateSolvent
HCID 10906Tert-Butyl nitriteSolvent
HCID 312751,4-DioxaneSolvent

Procedure

2.9 ml of 5.6 N HCl in dioxan and 0.67 ml of tert. butyl nitrite are added at -20° to a solution of 3.2 g of Z-Trp-Ala-Ser-Gly-NHNH2 in 50 ml of DMF. After standing 15 minutes at -20° 1.89 of L-Asparaginol hydrochloric and 2.5 ml of triethylamine are added. After standing for 15 hours at room temperature the reaction mixture is considerably reduced in volume, diluted with ethyl acetate and washed with dilute aqueous hydrochloride acid and with water. The title compound precipitates from the concentrated solution.

Workup

  1. waitAfter standing for 15 hours at room temperature
  2. washwashed with dilute aqueous hydrochloride acid and with water
  3. customThe title compound precipitates from the concentrated solution

Sources & evidence

ORD record
ord-e30be469581b413b98346acc682ad5bd
Source dataset
uspto-grants-1980_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04187295

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes