Diisopropylethylamine → {(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

HRID 1765933Notes

Reaction equation

HRID 1765933 reaction equation
FC(F)(F)C([O-])=O.[CH3:8][CH:9]([CH3:26])[CH2:10][C@@H:11]([NH3+:25])[B:12]1[O:20][C@H:19]2[C@:14]([CH3:24])([C@H:15]3[CH2:21][C@@H:17]([CH2:18]2)[C:16]3([CH3:23])[CH3:22])[O:13]1.[C:27]([NH:34][C@H:35]([C:39](O)=[O:40])[CH:36]([CH3:38])[CH3:37])([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28].CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.CCN(C(C)C)C(C)C>CN(C=O)C>[C:30]([O:29][C:27](=[O:28])[NH:34][C@H:35]([C:39](=[O:40])[NH:25][C@H:11]([B:12]1[O:20][C@H:19]2[C@:14]([CH3:24])([C@H:15]3[CH2:21][C@@H:17]([CH2:18]2)[C:16]3([CH3:23])[CH3:22])[O:13]1)[CH2:10][CH:9]([CH3:26])[CH3:8])[CH:36]([CH3:37])[CH3:38])([CH3:31])([CH3:33])[CH3:32]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 83693Boc-L-ValineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 20823732(S)-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)-butylammonium trifluoroacetate

Product 1

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

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The title compound is prepared as described in step B of example 1 but using (S)-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)-butylammonium trifluoroacetate ((C) in Synthetic Scheme 1) (for preparation see Kettner, C. A. and Shenvi, A. B. J. Biol. Chem. 1984, 259, p. 15106–15114 and Matteson, D. S. and Sadhu, K. M. J. Am. Chem. Soc. 1981, 103, p. 5241–5242) (2.395 g, 6.32 mMol), Boc-L-valine (1.373 g, 6.32 mMol), TBTU (2.23 g, 6.95 mMol, 1.1 equiv), DIEA (3.3 mL, 18.95 mMol, 3.0 equiv) and DMF (24 mL).

Workup

  1. customfor preparation

Sources & evidence

ORD record
ord-1f2607b1251846ad818b2f97ba542236
Source dataset
uspto-grants-2007_06
Patent number
US07229617B2

Reaction notes

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