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1,2-Dichloroethane → (S)-S-3-(benzyloxycarbonylamino)-4-(5-hydroxypentylamino)-4-oxobutyl ethanethioate

HRID 529495
Notes
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Reaction equation

HRID 529495 reaction equation
[C:1]([S:4][CH2:5][CH2:6][C@H:7]([NH:11][C:12]([O:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[O:13])[C:8]([OH:10])=O)(=[O:3])[CH3:2].[NH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][OH:28].C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1>CCOC(C)=O.C(Cl)Cl>[C:1](=[O:3])([S:4][CH2:5][CH2:6][C@H:7]([NH:11][C:12]([O:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[O:13])[C:8]([NH:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][OH:28])=[O:10])[CH3:2]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 111,2-DichloroethaneHCID 756345-Aminopentan-1-olHCID 757711-HydroxybenzotriazoleHCID 10757408(2S)-4-(acetylsulfanyl)-2-{[(benzyloxy)carbonyl]amino}butanoic acid

Product 1

HCID 86706209(S)-S-3-(benzyloxycarbonylamino)-4-(5-hydroxypentylamino)-4-oxobutyl ethanethioateYield 78.4%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a round bottom flask was added (S)-4-(acetylthio)-2-(benzyloxycarbonylamino)butanoic acid (312 mg, 1.00 mmol), 5-aminopentan-1-ol (119 mg, 1.15 mmol), DCM (5 mL), EDC (211 mg, 1.10 mmol) and HOBt (184 mg, 1.20 mmol). The light yellow mixture was stirred at rt for 16 hr. The reaction mixture was diluted with EtOAc (60 mL), washed with 5% aqueous KHSO4 (2×), saturated aqueous NaHCO3 (2×), water, and saturated aqueous NaCl. The organic layer was separated, dried over Na2SO4, filtered and concentrated. The residue was purified using silica gel chromatography (ISCO system) eluting with a gradient of 0-100% EtOAc/Hex to give (S)—S-3-(benzyloxycarbonylamino)-4-(5-hydroxypentylamino)-4-oxobutyl ethanethioate (311 mg, 0.784 mmol, 78% yield) as a white solid. Anal. Calcd. for C19H28N2O5S m/z 396.5. found: 397.3 (M+H)+; 1H NMR (400 MHz, CDCl3) δ ppm 7.47-7.28 (m, 5H), 6.41 (s, 1H), 5.59 (d, J=6.7 Hz, 1H), 5.11 (s, 2H), 4.13 (d, J=6.7 Hz, 1H), 3.63 (dd, J=11.6, 6.1 Hz, 2H), 3.28 (dd, J=12.7, 6.3 Hz, 2H), 2.97 (dt, J=14.5, 7.4 Hz, 1H), 2.91-2.75 (m, 1H), 2.34 (s, 3H), 2.21-2.00 (m, 1H), 1.91 (dt, J=14.4, 7.2 Hz, 1H), 1.72-1.48 (m, 5H), 1.48-1.34 (m, 2H).

Workup

  1. washwashed with 5% aqueous KHSO4 (2×), saturated aqueous NaHCO3 (2×), water, and saturated aqueous NaCl
  2. customThe organic layer was separated
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified
  7. washeluting with a gradient of 0-100% EtOAc/Hex

Sources & evidence

ORD record
ord-cb2bb04de0b1467ab76a482501762daf
Source dataset
uspto-grants-2016_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09346852B2

Reaction notes

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