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Triethylamine → HCID 57687746, compound

HRID 1880819
Notes
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Reaction equation

HRID 1880819 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]([C:19]#[N:20])=[CH:15][CH:14]=1)(=[O:12])=[O:11])[CH2:7][OH:8].F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.C(N(CC)CC)C.[CH3:59][O:60][C:61]([NH:63][C@@H:64]([CH:68]([C:75]1[CH:80]=[CH:79][CH:78]=[CH:77][CH:76]=1)[C:69]1[CH:74]=[CH:73][CH:72]=[CH:71][CH:70]=1)[C:65](O)=[O:66])=[O:62]>C(Cl)Cl>[CH3:59][O:60][C:61](=[O:62])[NH:63][C@H:64]([C:65](=[O:66])[NH:1][CH2:2][CH2:3][CH2:4][CH2:5][C@H:6]([N:9]([S:10]([C:13]1[CH:14]=[CH:15][C:16]([C:19]#[N:20])=[CH:17][CH:18]=1)(=[O:12])=[O:11])[CH2:21][CH:22]([CH3:24])[CH3:23])[CH2:7][OH:8])[CH:68]([C:75]1[CH:80]=[CH:79][CH:78]=[CH:77][CH:76]=1)[C:69]1[CH:74]=[CH:73][CH:72]=[CH:71][CH:70]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 10017620(S)-2-methoxycarbonylamino-3,3-diphenyl-propionic acidHCID 67530865HCID 67530865, compound

Product 1

HCID 57687746HCID 57687746, compoundYield 84%

Reagents, catalysts & solvents

1
HCID 6344DichloromethaneSolvent

Procedure

(S)—N-(5-Amino-1-hydroxymethyl-pentyl)-4-cyano-N-isobutyl-benzenesulfonamide (6) obtained in the previous reaction was dissolved in 50 mL CH2Cl2. BOP (1.2 eq), and triethylamine (5 eq) were added. After 10 minutes, (S)-2-methoxycarbonylamino-3,3-diphenyl-propionic acid (1 eq) was added and the mixture was stirred at RT for 3 hours. LCMS indicated a complete reaction. The reaction mixture was washed with sat. NaHCO3. The aqueous phase was washed again with 100 mL CH2Cl2. The combined organic layers where dried with MgSO4, filtered over dicalite and evaporated to dryness. The residue was purified by column chromatography with CH2Cl2-MeOH(NH3) (97:3). The appropriate fraction was evaporated to dryness. (1.31 g, 84% yield over 2 steps)

Workup

  1. customa complete reaction
  2. washThe reaction mixture was washed with sat. NaHCO3
  3. washThe aqueous phase was washed again with 100 mL CH2Cl2
  4. dry with materialThe combined organic layers where dried with MgSO4
  5. filtrationfiltered over dicalite
  6. customevaporated to dryness
  7. customThe residue was purified by column chromatography with CH2Cl2-MeOH(NH3) (97:3)
  8. customThe appropriate fraction was evaporated to dryness

Sources & evidence

ORD record
ord-31b13a880c4f4c4193747ff301fcfcd8
Source dataset
uspto-grants-2012_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08318779B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes