Hydrochloric Acid → HCID 131713448, compound

HRID 1904036Notes

Reaction equation

HRID 1904036 reaction equation
Cl.N(OC(C)(C)C)=O.[NH:9]([C:31]([O:33][CH2:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)=[O:32])[C@H:10]([C:17]([NH:19][C@H:20]([C:27]([NH:29]N)=[O:28])[CH2:21][O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:18])[CH2:11][O:12][C:13]([CH3:16])([CH3:15])[CH3:14].N[C@H:42]([C:47]([NH:49][C@H:50]([C:52]([O:54][CH3:55])=[O:53])[CH3:51])=[O:48])[CH2:43][C:44](=[O:46])[NH2:45].C(N1CCOCC1)C>C(OCC)(=O)C.CN(C)C=O>[NH:9]([C:31]([O:33][CH2:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)=[O:32])[C@H:10]([C:17]([NH:19][C@H:20]([C:27]([NH:29][C@H:42]([C:47]([NH:49][C@H:50]([C:52]([O:54][CH3:55])=[O:53])[CH3:51])=[O:48])[CH2:43][C:44](=[O:46])[NH2:45])=[O:28])[CH2:21][O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:18])[CH2:11][O:12][C:13]([CH3:16])([CH3:15])[CH3:14]

Participants

8

Reactant 5

HCID 313Hydrochloric Acid2×HCID 7525EthylmorpholineHCID 10906Tert-Butyl nitriteHCID 57241904HCID 57241904, compoundHCID 131713449HCID 131713449, compound

Product 1

HCID 131713448HCID 131713448, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

61.8 ml of 2.32 N-hydrochloric acid in ethyl acetate and 7.3 ml of tert.butyl nitrite are added to 25.95 g of Z-Ser(But)-Ser(But)-NH-NH2 in 200 ml of dimethylformamide at -10°. After 10 minutes a solution of 14.8 g of HCl.H-Asn-Ala-OMe and 36.16 ml of N-ethyl morpholine in 150 ml of dimethylformamide is added dropwise and the mixture is then kept for one hour at -10° and 15 hours at 0°. The solution is freed from the solvent by evaporation, the residue is taken up in chloroform and washed with sodium bicarbonate, dilute hydrochloric acid and with water. The Z-Ser(But)-Ser(But)-Asn-Ala-OCH3 obtained after evaporation of the solvent is reprecipitated from chloroform-petroleum ether. The Rf-value on silicagel in the system chloroform-methanol 9:1 is 0.35.

Workup

  1. customThe solution is freed from the solvent by evaporation
  2. washwashed with sodium bicarbonate, dilute hydrochloric acid and with water

Sources & evidence

ORD record
ord-24413d1935af42908cba349a5c6c52b6
Source dataset
uspto-grants-1984_03
Patent number
US04439425

Reaction notes

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