Triethylamine → HCID 21075128, compound

HRID 1171510Notes

Reaction equation

HRID 1171510 reaction equation
[O:1]1[C:5]2([CH2:10][CH2:9][CH:8]([NH2:11])[CH2:7][CH2:6]2)[O:4][CH2:3][CH2:2]1.[C:12]([NH:22][C@H:23]([C:28](O)=[O:29])[CH2:24][CH2:25][S:26][CH3:27])([O:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[O:13].O.ON1C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC.C(N(CC)CC)C>C(Cl)Cl>[CH2:15]([O:14][C:12]([NH:22][C@@H:23]([CH2:24][CH2:25][S:26][CH3:27])[C:28]([NH:11][CH:8]1[CH2:9][CH2:10][C:5]2([O:4][CH2:3][CH2:2][O:1]2)[CH2:6][CH2:7]1)=[O:29])=[O:13])[C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 1550857Benzyloxycarbonyl-L-methionineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 146343151,4-Dioxaspiro[4.5]decan-8-amine

Product 1

HCID 21075128HCID 21075128, compoundYield 64.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1,4-Dioxaspiro[4.5]decan-8-amine (5.03 g, 32.0 mmol, 1 eq.), CBZ-L-methionine (10.90, 38.4 mmol, 1.2 eq.), 1-hydroxybenzotriazole hydrate (HOBT) (5.19 g, 38.4 mmol, 1.2 eq.), 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide HCl (EDCI) (7.36 g, 38.4 mmol, 1.2 eq.), triethylamine (8.92 mL, 64.0 mmol, 2 eq.) and methylene chloride (150 mL) were stirred at room temperature under nitrogen for 72 hours. Worked up by rinsing 3 times with saturated sodium bicarbonate (50 mL). The organic layer was dried over sodium sulfate and stripped to give an amber oil which solidified. The solids were triturated with diethyl ether (100 mL) and stirred overnight. The solids were filtered to give 8-((2S)-2-(benzyloxycarbonylamino)-4-(methylthio)butanamido)-1,4-dioxaspiro[4.5]decane (8.75 g) as a white solid. Yield=64%. Mass Spec (ESI) detects (M+H)+=423.22.

Workup

  1. washby rinsing 3 times with saturated sodium bicarbonate (50 mL)
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. customto give an amber oil which
  4. customThe solids were triturated with diethyl ether (100 mL)
  5. filtrationThe solids were filtered

Sources & evidence

ORD record
ord-49d946410fed46e1b8b4400054c26123
Source dataset
uspto-grants-2010_11
Patent number
US07829571B2

Reaction notes

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