Dicyclohexylcarbodiimide → HCID 53935213, compound

HRID 1086593Notes

Reaction equation

[NH2:1][CH:2]([C:10]([OH:12])=[O:11])[CH2:3][CH:4]=[CH:5][CH2:6][C:7]([OH:9])=[O:8].C([NH:20][C@H:21]([C:23](O)=[O:24])[CH3:22])(OC(C)(C)C)=O.C1(N=C=NC2CCCCC2)CCCCC1>C(COC)OC>[NH2:20][C@H:21]([C:23]([NH:1][CH:2]([C:10]([OH:12])=[O:11])[CH2:3][CH:4]=[CH:5][CH2:6][C:7]([OH:9])=[O:8])=[O:24])[CH3:22]

Participants

Conditions

Temperature: 0 °C

Procedure

3.9 g of the product of Step D of Example 5 were dissolved in 200 ml of dimethoxyethane and 3.63 g of N-Boc-L-alanine were added. The mixture was cooled to -5°/0° C. and after addition of 3.99 g of dicyclohexylcarbodiimide, the mixture was vigorously stirred for 16 hours at 0° C. followed by filtering and evaporating to dryness. The residue was taken up in dimethoxyethane and filtered, then evaporated to dryness and taken up in methylene chloride. After washing with a saturated solution of sodium bicarbonate, then with salt water, drying and evaporating to dryness, 7.7 g of crude product were obtained which was chromatographed on silica. Elution with a cyclohexane - ethyl acetate mixture (7-3) yielded 5.4 g of the expected product with a specific roation of [α]=-18.5°±1° (c=1.6% in CH2Cl2).

Workup

filtrationby filtering
customevaporating to dryness
filtrationfiltered
customevaporated to dryness
washAfter washing with a saturated solution of sodium bicarbonate
dry with materialwith salt water, drying
customevaporating to dryness
custom7.7 g of crude product were obtained which
customwas chromatographed on silica
washElution with a cyclohexane - ethyl acetate mixture (7-3)

Sources & evidence

ORD record: ord-6209c2fdee924ce5a7a1d05bbaf70f49
Source dataset: uspto-grants-1991_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05030715

Reaction notes

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