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Methanol → (S)-2-(tert-butoxycarbonyl)-3-(2-nitro-N-(pent-4-enyl)phenylsulfonamido)propanoic acid

HRID 346963
Notes
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Reaction equation

HRID 346963 reaction equation
[C:1]([O:5][C:6]([C@@H:8]([CH2:13][N:14]([CH2:27][CH2:28][CH2:29][CH:30]=[CH2:31])[S:15]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[N+:24]([O-:26])=[O:25])(=[O:17])=[O:16])[C:9]([O:11]C)=[O:10])=[O:7])([CH3:4])([CH3:3])[CH3:2].C1COCC1.CO.[OH-].[Li+]>O>[C:1]([O:5][C:6]([C@@H:8]([CH2:13][N:14]([CH2:27][CH2:28][CH2:29][CH:30]=[CH2:31])[S:15]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[N+:24]([O-:26])=[O:25])(=[O:17])=[O:16])[C:9]([OH:11])=[O:10])=[O:7])([CH3:2])([CH3:4])[CH3:3]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 887MethanolHCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 21080148HCID 21080148, compound

Product 1

HCID 21080146(S)-2-(tert-butoxycarbonyl)-3-(2-nitro-N-(pent-4-enyl)phenylsulfonamido)propanoic acidYield 91.7%

Reagents, catalysts & solvents 1

HCID 962
Water
Solvent

Procedure

(S)-methyl 2-(tert-butoxycarbonyl)-3-(2-nitro-N-(pent-4-enyl)phenylsulfonamido)-propanoate iv (500 mg, 1.06 mmol) was dissolved in the mixed solvent system: THF (4 mL), methanol (1 mL), and water (2 mL). Powdered lithium hydroxide (250 mg, 10.4 mmol) was added. The light yellow slurry was stirred at rt for 15 h, and then concentrated in vacuo. The residue was partitioned between ether and water. The ether phase was discarded, and the aqueous phase was treated with 1 N HCl until the pH was 4. This acidic solution was extracted with ethyl acetate four times. The combined ethyl acetate extracts were dried (MgSO4) and concentrated in vacuo to give 430 mg (89%) of (S)-2-(tert-butoxycarbonyl)-3-(2-nitro-N-(pent-4-enyl)phenylsulfonamido)propanoic acid v as a yellow oil. 1H NMR (CD3OD, 300 MHz) δ 1.38 (s, 9H), 1.51–1.60 (m, 2H), 1.89–1.98 (m, 2H), 3.28–3.32 (m, 2H), 3.59–3.64 (dd, J=14.95, 9.46 Hz, 1H), 3.71–3.74 (m, 1H), 4.33 (dd, J=9.61, 4.43 Hz, 1H), 4.87–4.94 (m, 2H), 5.63–5.72 (m, 1H), 7.71–7.77 (m, 3H), 8.01 (dd, J=7.48, 1.37 Hz, 1H). LC-MS (Method D, retention time: 2.04 min), MS m/z 358 (M++1-Boc).

Workup

  1. concentrationconcentrated in vacuo
  2. customThe residue was partitioned between ether and water
  3. additionthe aqueous phase was treated with 1 N HCl until the pH was 4
  4. extractionThis acidic solution was extracted with ethyl acetate four times
  5. dry with materialThe combined ethyl acetate extracts were dried (MgSO4)
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-9aa9ce8123ce44d59f0021d2134c4151
Source dataset
uspto-grants-2007_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07173004B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes