Hydrochloric Acid → HCID 68283380, compound

HRID 1527554Notes

Reaction equation

HRID 1527554 reaction equation
[C:1]([N:8]1[CH2:15][CH2:14][CH2:13][C@H:9]1[C:10]([OH:12])=O)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[CH:16]([C:19]1[CH:23]=[C:22]([NH2:24])[O:21][N:20]=1)([CH3:18])[CH3:17].CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N=P1(N(CC)CC)N(C)CCCN1C)(C)(C)C.Cl>CN(C=O)C>[C:4]([O:3][C:1]([N:8]1[CH2:15][CH2:14][CH2:13][C@H:9]1[C:10](=[O:12])[NH:24][C:22]1[O:21][N:20]=[C:19]([CH:16]([CH3:18])[CH3:17])[CH:23]=1)=[O:2])([CH3:5])([CH3:6])[CH3:7]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 850831,2-Pyrrolidinedicarboxylic acid, 1-(1,1-dimethylethyl) ester, (2S)-HCID 21152083-(Propan-2-yl)-1,2-oxazol-5-amineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 35138512-((1,1-Dimethylethyl)imino)-N,N-diethylhexahydro-1,3-dimethyl-2lambda5-1,3,2-diazaphosphorin-2-amine

Product 1

HCID 68283380HCID 68283380, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of Boc-L-proline (150 mg, 0.697 mmol), 3-isopropylisoxazol-5-amine (88 mg, 0.697 mmol) and HBTU (264 mg, 0.697 mmol) in DMF (7 mL) was added 2-tert-butylimino-2-diethylamino-1,3-dimethylperhydro-1,3,2-diazaphosphorine (BEMP) (201 μl, 0.697 mmol) and the reaction mixture was stirred at RT under nitrogen for 48 h. The mixture was poured into HCl 1N and extracted three times with EtOAc. The combined organic layers were washed with an aqueous saturated solution of NaHCO3, with water, dried over Na2SO4, filtered and concentrated. The crude residue was purified by flash column chromatography on silica gel (c-hexane to c-hexane/EtOAc 7-3) to give the title compound. TLC, Rf (c-hexane/EtOAc 1:1)=0.6; MS (LC-MS): 324.1 [M+H]+, 346.1 [M+Na]+, 669.2 [2M+Na]+, 322.1 [M−H]−; tR (HPLC conditions a): 3.42 min.

Workup

  1. extractionextracted three times with EtOAc
  2. washThe combined organic layers were washed with an aqueous saturated solution of NaHCO3, with water
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude residue was purified by flash column chromatography on silica gel (c-hexane to c-hexane/EtOAc 7-3)

Sources & evidence

ORD record
ord-0a34270644e24ea2a97a7f70d3b46811
Source dataset
uspto-grants-2015_07
Patent number
US09085555B2

Reaction notes

Loading…