Tetrahydrofuran → HCID 70000374, compound

HRID 1264421Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:33]=[CH:32][C:6]([CH2:7][S:8][C@H:9]2[CH2:13][N:12]([S:14]([C:17]3[CH:26]=[CH:25][C:24]4[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=4)[CH:18]=3)(=[O:16])=[O:15])[C@H:11]([CH2:27][CH2:28][C:29]([OH:31])=O)[CH2:10]2)=[CH:5][CH:4]=1.[CH2:34]1[CH2:38]O[CH2:36][CH2:35]1.CCN=C=N[CH2:44][CH2:45][CH2:46][N:47]([CH3:49])C.C1C=CC2N(O)N=NC=2C=1>CCOC(C)=O>[CH2:46]([N:47]([CH3:49])[C:29](=[O:31])[CH2:28][CH2:27][C@@H:11]1[CH2:10][C@@H:9]([S:8][CH2:7][C:6]2[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:33][CH:32]=2)[CH2:13][N:12]1[S:14]([C:17]1[CH:26]=[CH:25][C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH:18]=1)(=[O:15])=[O:16])[C:45]1[CH:44]=[CH:36][CH:35]=[CH:34][CH:38]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To 75 mg (0.154 mmol, 1 eq) (2R,4R)-3-[4-(4-Methoxy-benzylsulfanyl)-1-(naphthalene-2-sulfonyl)-pyrrolidin-2-yl]-propionic acid in 0.86 ml THF 24 μl (0.185 mmol, 1.2 eq) benzyl methylamine were added, the solution was cooled to 0° C. and 71 mg (0.371 mmol, 2.4 eq) EDCI and 21 mg (0.151 mmol, 1.2 eq) HOBT were added. The mixture was stirred at RT over night, diluted with EtOAc and washed with 10% KHSO4, sat NaHCO3 solution and brine, dried over Na2SO4 and evaporated, yielding 131 mg (50%) (2R,4R)-N-Benzyl-3-[4-(4-methoxy-benzylsulfanyl)-1-(naphthalene-2-sulfonyl)-pyrrolidin-2-yl]-N-methyl-propionamide as brown gum, which was subjected to deprotection without further purification.

Workup

washwashed with 10% KHSO4
dry with materialdried over Na2SO4
customevaporated

Sources & evidence

ORD record: ord-869e5e55406f49339d6c392b6732b379
Source dataset: uspto-grants-2003_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06541638B2

Reaction notes

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