Triethylamine → 4-{2-[(Morpholine-4-carbonyl)-amino]-3-phenylmethanesulfonyl-propionylamino}-3-oxo-azepane-1-carboxylic acid benzyl ester

HRID 460408Notes

Reaction equation

HRID 460408 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:17][CH2:16][CH2:15][CH:14]([NH:18][C:19](=[O:41])[CH:20]([NH:32][C:33]([N:35]2[CH2:40][CH2:39][O:38][CH2:37][CH2:36]2)=[O:34])[CH2:21][S:22]([CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)(=[O:24])=[O:23])[CH:13]([OH:42])[CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C>CS(C)=O>[CH2:1]([O:8][C:9]([N:11]1[CH2:17][CH2:16][CH2:15][CH:14]([NH:18][C:19](=[O:41])[CH:20]([NH:32][C:33]([N:35]2[CH2:40][CH2:39][O:38][CH2:37][CH2:36]2)=[O:34])[CH2:21][S:22]([CH2:25][C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=2)(=[O:24])=[O:23])[C:13](=[O:42])[CH2:12]1)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 8471TriethylamineHCID 694406053-Hydroxy-4-{2-[(morpholine-4-carbonyl)-amino]-3-phenylmethanesulfonyl-propionylamino}-azepane-1-carboxylic acid benzyl ester

Product 1

HCID 694495704-{2-[(Morpholine-4-carbonyl)-amino]-3-phenylmethanesulfonyl-propionylamino}-3-oxo-azepane-1-carboxylic acid benzyl esterYield 74.8%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

3-Hydroxy-4-{2-[(morpholine-4-carbonyl)-amino]-3-phenylmethanesulfonyl-propionylamino}-azepane-1-carboxylic acid benzyl ester (100 mg, 0.167 mmol) was dissolved in DMSO (5 mL). Triethylamine (0.3 mL) and then SO3 pyridine complex (150 mg) were added and the mixture was stirred at ambient temperature for 3 hours. After dilution with ethyl acetate (100 mL), the solution was washed with water (50 mL) and brine, dried with MgSO4 and evaporated under vacuum. The residue was purified by flash chromatography on silica gel (Eluent: 5% methanol in ethyl acetate) to yield 4-{2-[(morpholine-4-carbonyl)-amino]-3-phenylmethanesulfonyl-propionylamino}-3-oxo-azepane-1-carboxylic acid benzyl ester (75 mg); 1H NMR: (DMSO) 8.23–8.08 (m, 1H), 7.40–7.29 (m, 10H), 7.06–6.98 (m, 1H), 5.20–5.09 (m, 2H), 4.79–4.65 (m, 1), 4.52–4.31 (m, 3H), 4.02–3.80 (m, 2H), 3.62–3.23 (m, 11H), 3.00–2.78 (m, 1H), 1.88–1.55 (m, 4H); MS: (M+H)+ 601.

Workup

  1. washAfter dilution with ethyl acetate (100 mL), the solution was washed with water (50 mL) and brine
  2. dry with materialdried with MgSO4
  3. customevaporated under vacuum
  4. customThe residue was purified by flash chromatography on silica gel (Eluent: 5% methanol in ethyl acetate)

Sources & evidence

ORD record
ord-f06e7fbdb84647ac87b7e5c0b586e4ca
Source dataset
uspto-grants-2007_03
Patent number
US07196099B2

Reaction notes

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