Dicyclohexylcarbodiimide → HCID 66725082, compound

HRID 1799218Notes

Reaction equation

HRID 1799218 reaction equation
C([NH:8][C@H:9]([C:11](O)=[O:12])[CH3:10])(OC(C)(C)C)=O.C1(N=C=NC2CCCCC2)CCCCC1.ON1C(=O)CCC1=O.Cl.[NH2:38][CH2:39][C@@H:40]([C:45]1[CH:50]=[CH:49][C:48]([Cl:51])=[C:47]([O:52][CH2:53][C:54]2[CH:59]=[CH:58][N:57]=[CH:56][CH:55]=2)[CH:46]=1)[CH2:41][C:42]([OH:44])=[O:43].C(=O)(O)[O-].[Na+]>C(#N)C.O>[ClH:51].[NH2:8][C@@H:9]([CH3:10])[C:11]([NH:38][CH2:39][C@@H:40]([C:45]1[CH:50]=[CH:49][C:48]([Cl:51])=[C:47]([O:52][CH2:53][C:54]2[CH:59]=[CH:58][N:57]=[CH:56][CH:55]=2)[CH:46]=1)[CH2:41][C:42]([OH:44])=[O:43])=[O:12]

Participants

8

Reactant 5

HCID 10868DicyclohexylcarbodiimideHCID 80170N-HydroxysuccinimideHCID 85082Tert-butoxycarbonylalanineHCID 516892Sodium BicarbonateHCID 66724763HCID 66724763, compound

Product 1

HCID 66725082HCID 66725082, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

Boc-alanine (0.37 mmol, 1 eq), N,N′-dicyclohexylcarbodiimide (0.47 mmol, 1.2 eq), and N-hydroxysuccinimide (0.47 mmol, 1.2 eq) were dissolved in 2 mL acetonitrile. The mixture was stirred at room temperature for 2 hr. The solid was filtered and added to (3R)-4-amino-3-[4-chloro-3-(4-pyridylmethoxy)phenyl]butanoic acid hydrochloride (68) and sodium bicarbonate (NaHCO3) (1.5 eq) in 1 mL water. The reaction was stirred at room temperature overnight. The solvent was then evaporated and treated with trifluoroacetic acid (TFA). The trifluoroacetic acid (TFA) was evaporated and purified by HPLC to provide the title compound (73). 1H-NMR (400 MHz, CD3OD): δ 8.53 (d, J=6.0 Hz, 2H), 7.57 (d, J=6.0 Hz, 2H), 7.30 (d, J=8.0 Hz, 1H), 7.05 (d, J=1.6 Hz, 1H), 6.87 (d, J=2 Hz, 1H), 5.26 (s, 2H), 3.69-3.74 (q, J=6.8 Hz, 1H), 3.56-3.61 (dd, J=8.4, 13.2 Hz, 1H), 3.28-3.39 (m, 1H), 2.55-2.61 (dd, J=16.0, 8.0 Hz, 1H), 2.44-2.50 (dd, J=15.2, 8.0 Hz, 1H), 1.23 (d, J=6.8, 3H); MS (ESI) m/z 391.87 (M+H)+.

Workup

  1. filtrationThe solid was filtered
  2. stirringThe reaction was stirred at room temperature overnight
  3. customThe solvent was then evaporated
  4. additiontreated with trifluoroacetic acid (TFA)
  5. customThe trifluoroacetic acid (TFA) was evaporated
  6. custompurified by HPLC

Sources & evidence

ORD record
ord-9ed9ecd7556f4cf086cbdea99b402f3d
Source dataset
uspto-grants-2013_01
Patent number
US08344028B2

Reaction notes

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