HCID 54000108, compound → HCID 86602159, compound

HRID 1711986Notes

Reaction equation

HRID 1711986 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([C:12]2[C:21]3[C:16](=[CH:17][CH:18]=[C:19]([O:22][CH3:23])[CH:20]=3)[CH:15]=[CH:14][C:13]=2[O:24][S:25]([C:28]([F:31])([F:30])[F:29])(=[O:27])=[O:26])=[N:4][N:3]=1.[NH2:32][C@@H:33]([C:40]([OH:45])([CH2:43][CH3:44])[CH2:41][CH3:42])[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1>>[CH2:41]([C:40]([OH:45])([CH2:43][CH3:44])[C@H:33]([NH:32][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([C:12]2[C:21]3[C:16](=[CH:17][CH:18]=[C:19]([O:22][CH3:23])[CH:20]=3)[CH:15]=[CH:14][C:13]=2[O:24][S:25]([C:28]([F:31])([F:30])[F:29])(=[O:27])=[O:26])=[N:4][N:3]=1)[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)[CH3:42]

Participants

3

Reactant 2

HCID 54000108HCID 54000108, compoundHCID 86602157HCID 86602157, compound

Product 1

HCID 86602159HCID 86602159, compound

Conditions

Temperature
120 °C

Procedure

To trifluoromethanesulfonic acid 1-(4-chlorophthalazin-1-yl)-7-methoxynaphthalen-2-yl ester (5.0 g, 11 mmol) was added 3-((R)-α-amino-benzyl)-pentan-3-ol (10 g, 52 mmol). The suspension was stirred for 18 hrs at 120° C. After cooling to 25° C., the mixture was filtered following addition of dichloromethane. The filtrate was concentrated under reduced pressure. The residue was purified by flash chromatography on silica gel (toluene/EtOAc 10:1 to 5:1) to give the title compound as a brown solid, which was triturated from hexane/diethyl ether to give 4.8 g (7.7 mmol) of a pure product as a mixture of diastereomers.

Workup

  1. temperatureAfter cooling to 25° C.
  2. filtrationthe mixture was filtered
  3. additionaddition of dichloromethane
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. customThe residue was purified by flash chromatography on silica gel (toluene/EtOAc 10:1 to 5:1)

Sources & evidence

ORD record
ord-e2629ed7a55949eeab7c6d2ef941d00a
Source dataset
uspto-grants-2010_09
Patent number
US07790882B2

Reaction notes

Loading…