Water → HCID 90060615, compound

HRID 1055392Notes

Reaction equation

HRID 1055392 reaction equation
Cl.[NH2:2][CH:3]1[C:9](=[O:10])[NH:8][C:7]2[CH:11]=[CH:12][CH:13]=[CH:14][C:6]=2[S:5][CH2:4]1.[N:15]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])([CH3:21])[C@H:16]([C:18](O)=[O:19])[CH3:17].O.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C.C1C=CC2N(O)N=NC=2C=1.Cl>[O:10]=[C:9]1[CH:3]([NH:2][C:18](=[O:19])[C@@H:16]([N:15]([CH3:21])[C:22](=[O:23])[O:24][C:25]([CH3:26])([CH3:28])[CH3:27])[CH3:17])[CH2:4][S:5][C:6]2[CH:14]=[CH:13][CH:12]=[CH:11][C:7]=2[NH:8]1

Participants

8

Reactant 4

HCID 962WaterHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 7009590(2S)-2-(((tert-butoxy)carbonyl)(methyl)amino)propanoic acidHCID 42614160HCID 42614160, compound

Product 1

HCID 90060615HCID 90060615, compoundYield 270%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 6228DimethylformamideSolventHCID 757711-HydroxybenzotriazoleSolvent

Procedure

3-Amino-2,3-dihydro-1,5-benzothiazepin-4(5H)-one hydrochloride (1.0 g, 5.15 mmol, Eq: 1.00), BOC—N-Me-Ala-OH (1.26 g, 1.62 mmol, Eq: 1.2) and TEA (2.2 mL, 15.45 mmol, Eq: 3.00) were dissolved in DMF (30 mL) and HOBT.H2O (697 mg, 5.14 mmol, Eq: 1.20) and HBTU (2.34 g, 6.18 mmol, Eq: 1.20) were added. After 1 h 20 min. the mixture was diluted with 1 N HCl and extracted with EtOAc. The organic extracts were washed with 1 N NaOH, brine, dried over Na2SO4 and concentrated to afford the title compound (1.66 g, 85% yield) which was used without purification.

Workup

  1. extractionextracted with EtOAc
  2. washThe organic extracts were washed with 1 N NaOH, brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-91e24da3a02f4f8195c7113847b5340a
Source dataset
uspto-grants-2016_07
Patent number
US09394263B2

Reaction notes

Loading…