L-Leucine, N-((1,1-dimethylethoxy)carbonyl)- → {(S)-3-Methyl-1-[(R)-3-methyl-1-((1S,2S,6R,8S)-2,9,9-trimethyl-3,5-dioxa-4-bora-tricyclo[6.1.1.02,6]dec-4-yl)butylcarbamoyl]-butyl}-carbamic acid tert-butyl ester

HRID 585888Notes

Reaction equation

HRID 585888 reaction equation
C(OC(=O)N[C@H](C(=O)[NH:13][C@H:14]([B:19]1[O:27][C@H:26]2[C@:21]([CH3:31])([C@H:22]3[CH2:28][C@@H:24]([CH2:25]2)[C:23]3([CH3:30])[CH3:29])[O:20]1)[CH2:15][CH:16]([CH3:18])[CH3:17])C(C)C)(C)(C)C.[C:34]([NH:41][C@H:42]([C:47]([OH:49])=O)[CH2:43][CH:44]([CH3:46])[CH3:45])([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:35]>>[C:37]([O:36][C:34](=[O:35])[NH:41][C@H:42]([C:47](=[O:49])[NH:13][C@H:14]([B:19]1[O:27][C@H:26]2[C@:21]([CH3:31])([C@H:22]3[CH2:28][C@@H:24]([CH2:25]2)[C:23]3([CH3:29])[CH3:30])[O:20]1)[CH2:15][CH:16]([CH3:18])[CH3:17])[CH2:43][CH:44]([CH3:45])[CH3:46])([CH3:38])([CH3:39])[CH3:40]

Participants

3

Reactant 2

HCID 83170L-Leucine, N-((1,1-dimethylethoxy)carbonyl)-HCID 67492646{(S)-2-Methyl-1-[(R)-3-methyl-1-((1S,2S,6R,8S)-2,9,9-trimethyl-3,5-dioxa-4-bora-tricyclo[6.1.1.02,6]dec-4-yl)-butylcarbamoyl-]propyl}-carbamic acid tert-butyl ester

Product 1

HCID 67492464{(S)-3-Methyl-1-[(R)-3-methyl-1-((1S,2S,6R,8S)-2,9,9-trimethyl-3,5-dioxa-4-bora-tricyclo[6.1.1.02,6]dec-4-yl)butylcarbamoyl]-butyl}-carbamic acid tert-butyl ester

Procedure

The title compound is prepared as described for {(S)-2-Methyl-1-[(R)-3-methyl-1-((1S,2S,6R,8S)-2,9,9-trimethyl-3,5-dioxa-4-bora-tricyclo[6.1.1.02,6]dec-4-yl)-butylcarbamoyl]-propyl}-carbamic acid tert-butyl ester (example 1 (c)) but using Boc-L-leucine.

Sources & evidence

ORD record
ord-7780524ed2e24ece86fb2debc00592f2
Source dataset
uspto-grants-2005_08
Patent number
US06933290B2

Reaction notes

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