4-Iodobenzenesulfonyl chloride → HCID 69002742, compound

HRID 557463Notes

Reaction equation

C([O:5][C:6](=[O:30])[CH:7]([NH:17][C:18]([NH:20][CH:21]([C:27]([OH:29])=[O:28])[CH2:22][CH2:23][CH2:24][CH2:25][NH2:26])=[O:19])[CH2:8][CH2:9][C:10]([O:12]C(C)(C)C)=[O:11])(C)(C)C.O1CCOCC1.[I:37][C:38]1[CH:43]=[CH:42][C:41]([S:44](Cl)(=[O:46])=[O:45])=[CH:40][CH:39]=1>O>[C:27]([CH:21]([NH:20][C:18](=[O:19])[NH:17][CH:7]([CH2:8][CH2:9][C:10]([OH:12])=[O:11])[C:6]([OH:5])=[O:30])[CH2:22][CH2:23][CH2:24][CH2:25][NH:26][S:44]([C:41]1[CH:42]=[CH:43][C:38]([I:37])=[CH:39][CH:40]=1)(=[O:46])=[O:45])([OH:29])=[O:28]

Participants

Conditions

Temperature: 50 °C

Procedure

In a round bottom flask 2-[3-(5-Amino-1-carboxy-pentyl)-ureido]-pentanedioic acid di t-butyl ester (300 mg, 0.62 mmol) is suspended in water (10 mL) and 1,4 dioxane (10 mL) and TEA (1.75 mL, 1.25 mmol) was added followed by 4-iodo-benzenesulfonyl chloride and the mixture stirred overnight at 50° C. The reaction mixture was evaporated to dryness, taken up in DCM and chromatographed over silica gel to afford the desired product (375 mg, 80%) as a clear oil. The compound was deprotected using the previously described methods followed by HPLC purification to afford the desired product MIP-1097 as a whiter solid (270 grams, 90% yield). 1H NMR (400 MHz, DMSO-d6) δ 7.97 (d, 2H), 7.68 (t, 1H), 7.53 (d, 2H), 6.35 (dd, 2H), 4.10 (m, 1H), 4.00 (m, 1H), 2.65 (m, 2H), 2.22 (m, 2H), 1.9 (m, 1H), 1.7 (m, 1H), 1.55 (m, 1H), 1.45 (m, 1H), 1.35 (m, 2H), 1.25 (m, 2H), (3 CO2H not seen). ESMS m/z: 565 (M+H)+.

Workup

customThe reaction mixture was evaporated to dryness
customchromatographed over silica gel

Sources & evidence

ORD record: ord-515ddfb177e04b0bbea25fbf167f156e
Source dataset: uspto-grants-2011_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08058449B2

Reaction notes

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