Triethylamine → HCID 69027006, compound

HRID 1432898Notes

Reaction equation

HRID 1432898 reaction equation
[C:1]([NH:11][C@H:12]([C:16]([OH:18])=[O:17])[CH2:13][O:14][CH3:15])([O:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:2].CCN(CC)CC.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.[CH3:48][O:49][CH:50]([O:53][CH3:54])[CH2:51][NH2:52]>C(Cl)Cl.CCOCC>[C:1]([NH:11][C@H:12]([C:16]([OH:18])=[O:17])[CH2:13][O:14][CH3:15])([O:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:2].[CH3:48][O:49][CH:50]([O:53][CH3:54])[CH2:51][NH2:52]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 89728Aminoacetaldehyde dimethyl acetalHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 22824012N-[(Benzyloxy)carbonyl]-O-methyl-L-serine

Product 1

HCID 69027006HCID 69027006, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of N-Cbz-O-methylserine (10.8 g, 41.8 mmol) in 500 mL of CH2Cl2 is added Et3N (12.7 g, 125 mmol). The solution is cooled to 0° C. and TBTU (13.5 g, 42 mmol) and aminoacetaldehyde dimethyl acetal (4.83 g, 46 mmol) are added. The solution is stirred for 16 hours. The solution is diluted with 500 mL of ether. The resulting solution is washed with water, 1N KHSO4, and sat. NaCl. The title compound (13.7 g, 41.8 mmol) is obtained as a white foam. 1H NMR (CDCl3, 300 MHz) δ7.40 (m, 5H), 6.55 (bs, 1H), 5.66 (bs, 1H), 5.32 (m, 1H), 5.13 (s, 2H), 4.32 (m, 2H), 3.79 (dd, 1H), 3.44 (m, 2H), 3.40 (m, 9H).

Workup

  1. washThe resulting solution is washed with water, 1N KHSO4, and sat. NaCl

Sources & evidence

ORD record
ord-9a7ee57578eb412497a2d1e7fea8bb16
Source dataset
uspto-grants-2009_11
Patent number
US07612075B2

Reaction notes

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