Ammonium Chloride → HCID 86597944, compound

HRID 854653Notes

Reaction equation

HRID 854653 reaction equation
[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]

Participants

8

Reactant 4

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

Product 1

HCID 86597944HCID 86597944, compoundYield 99%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

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+).

Workup

  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

Sources & evidence

ORD record
ord-09f64f4ba2fe44ccb7115b1bf25fc90f
Source dataset
uspto-grants-2007_08
Patent number
US07259177B2

Reaction notes

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