Ammonium Chloride → HCID 86597944, Verbindung

HRID 854653

Reaktionsgleichung

Reaktionsgleichung von HRID 854653
[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:12]=[CH:11][C:10]([CH3:13])=[CH:9][CH:8]=2)=[N:4][C:3]=1[CH2:14][O:15][C@@H:16]1[CH2:21][CH2:20][CH2:19][C@H:18]([CH:22]=O)[CH2:17]1.[NH2:24][C@H:25]([C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[CH:26]([CH3:28])[CH3:27].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[NH4+].[Cl-]>ClCCl.O.CC(O)=O>[CH3:27][CH:26]([CH3:28])[C@H:25]([NH:24][CH2:22][C@H:18]1[CH2:19][CH2:20][CH2:21][C@@H:16]([O:15][CH2:14][C:3]2[N:4]=[C:5]([C:7]3[CH:8]=[CH:9][C:10]([CH3:13])=[CH:11][CH:12]=3)[O:6][C:2]=2[CH3:1])[CH2:17]1)[C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30]

Komponenten

8

Edukt 4

HCID 25517Ammonium ChlorideHCID 114626tert-Butyl L-valinateHCID 5049666Sodium triacetoxyborohydrideHCID 86597945cis-3-(5-Methyl-2-p-tolyloxazol-4-ylmethoxy)cyclohexanecarbaldehyde

Produkt 1

HCID 86597944HCID 86597944, VerbindungAusbeute 99 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 176Acetic AcidLösungsmittelHCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittel2×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

511 mg of cis-3-(5-methyl-2-p-tolyloxazol-4-ylmethoxy)cyclohexanecarbaldehyde, 0.9 ml of HOAc and 310 mg of tert-butyl (S)-valinate are dissolved in 5 ml of abs. dichloromethane. 500 mg of molecular sieve 4 Å are then added, and the suspension is cooled to 0° C. 414 mg of sodium triacetoxyborohydride are added a little at a time. This suspension is stirred at 0° C. for 2 h, 3 ml of saturated NH4Cl solution are then added and the suspension is stirred for a further 10 min. In each case 10 ml of water and dichloromethane are added, the phases are separated, the aqueous phase is extracted with dichloromethane and the combined organic phases are dried over MgSO4 and concentrated, which gives 760 mg of tert-butyl (S)-3-methyl-2-{[cis-3-(5-methyl-2-p-tolyloxazol-4-ylmethoxy)cyclohexylmethyl]-amino}butyrate. C28H42N2O4 (470.66); MS (ESI): 471.50 (MH+).

Aufarbeitung

  1. addition500 mg of molecular sieve 4 Å are then added
  2. stirringthe suspension is stirred for a further 10 min
  3. customthe phases are separated
  4. extractionthe aqueous phase is extracted with dichloromethane
  5. dry with materialthe combined organic phases are dried over MgSO4
  6. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-09f64f4ba2fe44ccb7115b1bf25fc90f
Quelldatensatz
uspto-grants-2007_08
Patentnummer
US07259177B2

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