IN2-(benzyloxycarbonyl)-N6-(tert-butoxycarbonyl)-L-lysine → HCID 14498534, compound

HRID 1880815Notes

Reaction equation

[CH2:1]([O:8][C:9]([NH:11][C@@H:12]([CH2:16][CH2:17][CH2:18][CH2:19][NH:20][C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[C:13](O)=[O:14])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>C1COCC1>[C:24]([O:23][C:21](=[O:22])[NH:20][CH2:19][CH2:18][CH2:17][CH2:16][C@H:12]([NH:11][C:9]([O:8][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)=[O:10])[CH2:13][OH:14])([CH3:27])([CH3:25])[CH3:26]

Participants

Conditions

Temperature: -10 °C

Procedure

Commercially available (S)-2-benzyloxycarbonylamino-6-tert-butoxycarbonylamino-hexanoic acid (1) (14.89 g) was dissolved in 120 mL dry THF. This solution was cooled to −10° C. BH3 (80 mL, 1M in THF) was slowly added and the resulting solution was stirred for 1 hour below −5° C. and was allowed to warm to room temperature overnight. The reaction was quenched with MeOH, evaporated to dryness and use as such in the next reaction.

Workup

temperatureto warm to room temperature overnight
customThe reaction was quenched with MeOH
customevaporated to dryness and use as
customsuch in the next reaction

Sources & evidence

ORD record: ord-fcefa16d7bfb41388d7df32e7e4c7f7f
Source dataset: uspto-grants-2012_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08318779B2

Reaction notes

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