Oxygen → HCID 10159194, compound

HRID 2119324Notes

Reaction equation

ON[C:3]([C@H:5]1[C:10]([CH3:12])([CH3:11])[S:9](=O)(=O)[CH2:8][CH2:7][N:6]1[S:15]([C:18]1[CH:23]=[CH:22][C:21]([C:24]2[CH:29]=[CH:28][C:27](Br)=[CH:26][CH:25]=2)=[CH:20][CH:19]=1)(=[O:17])=[O:16])=[O:4].[OH:31][CH2:32]C1C=CC(B(O)O)=CC=1.B(O)[OH:43].O=O>O1CCOCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[OH:31][CH2:32][C:27]1[CH:28]=[CH:29][C:24]([C:21]2[CH:22]=[CH:23][C:18]([S:15]([N:6]3[CH2:7][CH2:8][S:9][C:10]([CH3:12])([CH3:11])[C@@H:5]3[C:3]([OH:43])=[O:4])(=[O:17])=[O:16])=[CH:19][CH:20]=2)=[CH:25][CH:26]=1

Participants

Conditions

Temperature: 75 °C

Procedure

(S)-4-(4-Iodophenyl-1-sulfonyl)-2,2-dimethyl-thiomorpholine-3-carboxylic acid hydroxamide-O-Wang resin (15, Scheme 4) (5.0 g at 1 mmol/g loading, 5 mmol) was swelled in dioxane (40 mL). To this was added 4-hydroxymethylbenzene boronic acid (30 mL of a 0.5 M solution in dioxane/2.5 M aq. Na2CO3 [3 M equivalents relative to the boronic acid], 15 mmol). In a dry, oxygen free environment Pd(PPh3)4 (200 mg) was added, and the mixture was stirred while at 75° C. for 48 hours. Filtration and subsequent resin washing three times with alternating CH2Cl2 (20 mL) followed by THF (20 mL) gave the (S)-4-(4′-hydroxymethyl-biphenyl-4-sulfonyl)-2,2-dimethyl-thiomorpholine-3-carboxylic acid hydroxamide-O-Wang resin.

Workup

filtrationFiltration and subsequent resin
washwashing three times with alternating CH2Cl2 (20 mL)

Sources & evidence

ORD record: ord-7cb87bb2869d4b4bb22d8aea7c8cf937
Source dataset: uspto-grants-2004_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06686355B2

Reaction notes

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