Sulfuryl chloride → (1S,5S)-(1-{5-[(3-Amino-4-fluoro-benzenesulfonyl)-isobutyl-amino]-6-hydroxy-hexylcarbamoyl}-2-naphthalen-2-yl-ethyl)-carbamic Acid tert-Butyl Ester

HRID 987994Notes

Reaction equation

HRID 987994 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][CH2:5][C@H:6]([N:9]([CH2:21][CH:22]([CH3:24])[CH3:23])[S:10]([C:13]1[CH:18]=[CH:17][C:16]([F:19])=[C:15]([NH2:20])[CH:14]=1)(=[O:12])=[O:11])[CH2:7][OH:8].S(Cl)(Cl)(=O)=O.[C:30]([O:34][C:35]([NH:37][C@@H:38]([CH2:42][C:43]1[CH:52]=[CH:51][C:50]2[C:45](=[CH:46][CH:47]=[CH:48][CH:49]=2)[CH:44]=1)[C:39](O)=[O:40])=[O:36])([CH3:33])([CH3:32])[CH3:31]>>[C:30]([O:34][C:35](=[O:36])[NH:37][C@H:38]([C:39](=[O:40])[NH:1][CH2:2][CH2:3][CH2:4][CH2:5][C@H:6]([N:9]([S:10]([C:13]1[CH:18]=[CH:17][C:16]([F:19])=[C:15]([NH2:20])[CH:14]=1)(=[O:12])=[O:11])[CH2:21][CH:22]([CH3:24])[CH3:23])[CH2:7][OH:8])[CH2:42][C:43]1[CH:52]=[CH:51][C:50]2[C:45](=[CH:46][CH:47]=[CH:48][CH:49]=2)[CH:44]=1)([CH3:31])([CH3:33])[CH3:32]

Participants

4

Reactant 3

HCID 24648Sulfuryl chlorideHCID 7020908Boc-3-(2-naphthyl)-L-alanineHCID 67531641(1S)-N-(5-amino-1-hydroxymethyl-pentyl)-N-isobutyl-3-amino-4-fluoro-benzenesulfonamide

Product 1

HCID 514012(1S,5S)-(1-{5-[(3-Amino-4-fluoro-benzenesulfonyl)-isobutyl-amino]-6-hydroxy-hexylcarbamoyl}-2-naphthalen-2-yl-ethyl)-carbamic Acid tert-Butyl EsterYield 38%

Procedure

The title compound was prepared from the crude amine mixture of (1S)-N-(5-amino-1-hydroxymethyl-pentyl)-N-isobutyl-3-amino-4-fluoro-benzenesulfonamide which is described earlier (example 53, step C, which was made from a batch of sulfonyl chloride containing the two regioisomers) and (2S)-2-tert-butoxycarbonylamino-3-naphthalen-2-yl-propionic acid using general procedure A. The crude residue was purified by semi-preparative HPLC in several batches of 80 mg using a gradient of 35 to 90% of acetonitrile over 30 min and a flow rate of 15 mL/min, retention time=23.9 min. All the pure fractions were combined to provide 460 mg (38% yield) of the title compound.

Workup

  1. customThe crude residue was purified by semi-preparative HPLC in several batches of 80 mg
  2. customover 30 min

Sources & evidence

ORD record
ord-e9c8ac507a784ab08f8db9ab89dcb2c8
Source dataset
uspto-grants-2003_10
Patent number
US06632816B1

Reaction notes

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