Selectfluor → (1S,5S)-{1-[5-[(4-amino-3-fluoro-benzenesulfonyl)-isobutyl-amino]-6-(diethoxy-phosphoryloxy)-hexylcarbamoyl]-2,2-diphenyl-ethyl}-carbamic acid methyl ester

HRID 132701Notes

Reaction equation

HRID 132701 reaction equation
[CH3:1][O:2][C:3](=[O:45])[NH:4][CH:5]([C:19](=[O:44])[NH:20][CH2:21][CH2:22][CH2:23][CH2:24][CH:25]([N:28]([S:33]([C:36]1[CH:41]=[CH:40][C:39]([NH2:42])=[C:38]([F:43])[CH:37]=1)(=[O:35])=[O:34])[CH2:29][CH:30]([CH3:32])[CH3:31])[CH2:26][OH:27])[CH:6]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.COC(=O)N[C@H](C(=O)NCCCC[C@H:70](N(S(C1C=CC(N)=CC=1)(=O)=O)CC(C)C)[CH2:71][O:72][P:73]([OH:76])([OH:75])=O)C(C1C=CC=CC=1)C1C=CC=CC=1.[B-](F)(F)(F)F.[B-](F)(F)(F)F.[CH2:104]1[N+]2(CCl)CC[N+](F)(CC2)[CH2:105]1>CC#N>[CH3:1][O:2][C:3](=[O:45])[NH:4][C@H:5]([C:19](=[O:44])[NH:20][CH2:21][CH2:22][CH2:23][CH2:24][C@H:25]([N:28]([S:33]([C:36]1[CH:41]=[CH:40][C:39]([NH2:42])=[C:38]([F:43])[CH:37]=1)(=[O:34])=[O:35])[CH2:29][CH:30]([CH3:32])[CH3:31])[CH2:26][O:27][P:73]([O:72][CH2:71][CH3:70])([O:75][CH2:104][CH3:105])=[O:76])[CH:6]([C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 2724933SelectfluorHCID 11563875(1S,5S)-(1-{5-[(4-amino-benzenesulfonyl)-isobutyl-amino]-6-phosphonooxy hexylcarbamoyl}-2,2-diphenyl-ethyl)-carbamic acid methyl esterHCID 24815407(1-{5-[(4-Amino-3-fluoro-benzenesulfonyl)-isobutyl-amino]-6-hydroxy-hexylcarbamoyl}-2,2-diphenyl-ethyl)-carbamic acid methyl ester

Product 1

HCID 66791048(1S,5S)-{1-[5-[(4-amino-3-fluoro-benzenesulfonyl)-isobutyl-amino]-6-(diethoxy-phosphoryloxy)-hexylcarbamoyl]-2,2-diphenyl-ethyl}-carbamic acid methyl esterYield 48%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

The product of step A above, (1S,5S)-(1-{5-[(4-amino-benzenesulfonyl)-isobutyl-amino]-6-phosphonooxy hexylcarbamoyl}-2,2-diphenyl-ethyl)-carbamic acid methyl ester (0.555 g, 0.73 mmol) was dissolved in 5 mL MeCN. Selectfluor (0.26 g, 0.7 mmol) was added and the mixture stirred for 30 min. The mixture was purified by reverse phase preparative HPLC and lyophilized to yield 278 mg (48% yield) white solid.

Workup

  1. customThe mixture was purified by reverse phase preparative HPLC

Sources & evidence

ORD record
ord-0f927b33c4964db392cfacb79be290ae
Source dataset
uspto-grants-2008_06
Patent number
US07388008B2

Reaction notes

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