Triethylamine → tert-butyl N-[(1S)-5-[(E)-N'-hydroxycarbamimidoyl]-1,2,3,4-tetrahydronaphthalen-1-yl]carbamate

HRID 1807574Notes

Reaction equation

HRID 1807574 reaction equation
[C:1]([C:3]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:4]=1[CH2:5][CH2:6][CH2:7][C@@H:8]2[NH:13][C:14](=[O:20])[O:15][C:16]([CH3:19])([CH3:18])[CH3:17])#[N:2].Cl.[NH2:22][OH:23].CCN(CC)CC>CCO>[OH:23][NH:22][C:1]([C:3]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:4]=1[CH2:5][CH2:6][CH2:7][C@@H:8]2[NH:13][C:14](=[O:20])[O:15][C:16]([CH3:18])([CH3:17])[CH3:19])=[NH:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 443297Hydroxyamine hydrochlorideHCID 58354989HCID 58354989, compound

Product 1

HCID 178453867tert-butyl N-[(1S)-5-[(E)-N'-hydroxycarbamimidoyl]-1,2,3,4-tetrahydronaphthalen-1-yl]carbamate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
85 °C

Procedure

Prepared using General Procedure 1. To a stirring solution of (S)-tert-butyl (5-cyano-1,2,3,4-tetrahydronaphthalen-1-yl)carbamate INT-8 (3.10 g, 11.38 mmol) in EtOH (25 mL) was added hydroxylamine hydrochloride (2.77 g, 39.84 mmol) and NEt3 (3.17 mL, 22.77 mmol). After heating at 85° C. for 15 h, the mixture was concentrated, redissolved in DCM, and washed with NaHCO3. The combined organic layers were dried, concentrated and chromatographed (MeOH/DCM) to provide 3.56 g crude (S)-tert-butyl (5-(N-hydroxycarbamimidoyl)-1,2,3,4-tetrahydronaphthalen-1-yl)carbamate INT-10 (58% product by UV area), which was used in the next reaction without further purification. LCMS-ESI (m/z) calculated for C16H23N3O3: 305.37; found 306.2 [M+H]+, tR=2.00 min.

Workup

  1. customPrepared
  2. concentrationthe mixture was concentrated
  3. dissolutionredissolved in DCM
  4. washwashed with NaHCO3
  5. customThe combined organic layers were dried
  6. concentrationconcentrated
  7. customchromatographed (MeOH/DCM)

Sources & evidence

ORD record
ord-404bdb1c618947e6841ff1ea9abfdebf
Source dataset
uspto-grants-2013_01
Patent number
US08357706B2

Reaction notes

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