Diisopropylethylamine → HCID 67772568, compound

HRID 1808809Notes

Reaction equation

HRID 1808809 reaction equation
CCN(C(C)C)C(C)C.[C:10]([O:14][C:15]([NH:17][C@@H:18]([CH3:22])[C:19]([OH:21])=O)=[O:16])([CH3:13])([CH3:12])[CH3:11].CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.Cl.[NH:46]1[CH2:49][CH:48]([OH:50])[CH2:47]1.C([O-])(O)=O.[Na+]>C(Cl)Cl>[OH:50][CH:48]1[CH2:49][N:46]([C:19](=[O:21])[C@@H:18]([NH:17][C:15](=[O:16])[O:14][C:10]([CH3:11])([CH3:12])[CH3:13])[CH3:22])[CH2:47]1

Participants

7

Reactant 5

HCID 81531DiisopropylethylamineHCID 85082Tert-butoxycarbonylalanineHCID 516892Sodium BicarbonateHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 27592903-Hydroxyazetidine hydrochloride

Product 1

HCID 67772568HCID 67772568, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

DIPEA (8.53 mL, 49.0 mmol) was added to a mixture of (S)-2-(tert-butoxycarbonylamino)propanoic acid (3.089 g, 16.33 mmol), which is commercially available, and TBTU (5.24 g, 16.33 mmol) in DCM (30 mL). Upon stirring at rt the mixture gradually became a clear solution. Azetidin-3-ol hydrochloride (2.68 g, 24.5 mmol) was added and the mixture was stirred over night. NaHCO3 (8% aq., 20 mL) was added. The organic layer was washed with NaHCO3 (8% aq., 3×60 mL). DCM (100 mL) was used for back extraction of the combined aqueous phases. Toluene was added and the combined organic layers were concentrated on the rotavapor over night (45° C. in waterbath) to give the title product (3.35 g, 84%,) as a transparent oil which solidified upon standing. Mixture of rotamers: 1H NMR (500 MHz, CD3OD) δ 1.21-1.27, 1.41-1.49, 3.7-3.83, 3.98-4.27, 4.41-4.47, 4.56-4.64.

Workup

  1. stirringthe mixture was stirred over night
  2. washThe organic layer was washed with NaHCO3 (8% aq., 3×60 mL)
  3. extractionDCM (100 mL) was used for back extraction of the combined aqueous phases
  4. additionToluene was added
  5. concentrationthe combined organic layers were concentrated on the rotavapor over night (45° C. in waterbath)

Sources & evidence

ORD record
ord-4e0ca8ccb6a2444ea96d2996c1f4e07f
Source dataset
uspto-grants-2013_01
Patent number
US08361998B2

Reaction notes

Loading…