L-Glutamine → Boc-L-Valine

HRID 2256808Notes

Reaction equation

HRID 2256808 reaction equation
N[C@H]([C:8]([OH:10])=[O:9])CCC(=O)N.[NH2:11][C@H:12]([C:17]([OH:19])=[O:18])[C@H:13]([CH2:15]C)[CH3:14].N1CCC[C@H]1C(O)=O.N[C@H](C(O)=O)[C@@H](C)O.N[C@H](C(O)=O)[CH2:38][C:39]1[C:47]2C(=CC=CC=2)N[CH:40]=1.C(S)CS>>[C:8]([NH:11][C@H:12]([C:17]([OH:19])=[O:18])[CH:13]([CH3:14])[CH3:15])([O:10][C:39]([CH3:47])([CH3:40])[CH3:38])=[O:9]

Participants

7

Reactant 6

HCID 5961L-Glutamine2×HCID 6288L-ThreonineHCID 6305L-TryptophanHCID 6306L-IsoleucineHCID 109021,2-EthanedithiolHCID 145742L-Proline

Product 1

HCID 83693Boc-L-Valine

Procedure

A larger excess of 6 to 8 equivalents is used in the coupling of steps (h) and (m) with the tert-butoxycarbonyl-protected amino acids aparagine, glutamine, isoleucine, proline, and threonine. In the cycles following addition of a tryptophane residue, 2% 1,2-ethanedithiol (FLUKA) is added to the deprotection steps (a) and (b) in order to prevent the oxidation of the indole ring. Dehydration of the carboxamide function of glutamine is minimized by preforming the 1-hydroxybenzotriazole ester (0°, 15 min) before addition to the resin in step (h).

Workup

  1. additionbefore addition to the resin in step (h)

Sources & evidence

ORD record
ord-c03513d166bf4d9d933f5a2eda0b8657
Source dataset
uspto-grants-1997_08
Patent number
US05656596

Reaction notes

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